ChemicalBook CAS DataBase List 5-(ADAMANT-1-YL-METHOXY)-PENTANAL

5-(ADAMANT-1-YL-METHOXY)-PENTANAL synthesis

14synthesis methods

Product Name:5-(ADAMANT-1-YL-METHOXY)-PENTANAL
CAS Number:202577-32-0
Molecular formula:C16H26O2
Molecular Weight:250.38

1-Pentanol, 5-(tricyclo[3.3.1.13,7]dec-1-ylmethoxy)-

857254-46-7
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202577-32-0
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Yield:202577-32-0 95%

Reaction Conditions:

Stage #1: 5-(adamantan-1-yl-methoxy)-1-pentanolwith oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -70; for 0.25 h;
Stage #2: with triethylamine at -70; for 0.0833333 h;
Stage #3: in dichloromethane at 20;

Steps:

4

A dry flask was charged with anhydrous CH2CI2 (25 mL) and oxalyl chloride (14. 1 mL, 28.2 mmol) under anhydrous N2. The mixture was cooled to-70 °C and a solution of dimethyl sulfoxide (DMSO, 3.09 mL, 43.5 mmol) in anhydrous CH2CI2 (5 mL) was added in a dropwise manner. After 5 min, compound lIa (3.23 g, 12.8 mmol) was added and the mixture was stirred for 15 min, becoming a milky yellow. Triethylamine (8.87 mL, 64.0 mmol) was added and the mixture stirred for 5 min, then allowed to warm to room temperature, followed by addition of H20 (50 mL) and extraction with CH2CI2. Drying and solvent removal from the combined extracts afforded compound 2 (3.04 g, 12.2 mmol) in 95% yield as a clear, colorless oil.

References:

WO2005/63706,2005,A1 Location in patent:Page 14

1,3-Dioxolane, 2-[4-(tricyclo[3.3.1.13,7]dec-1-ylmethoxy)butyl]-

1029378-70-8
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202577-32-0
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770-71-8
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202577-32-0
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Tricyclo[3.3.1.13,7]decane, 1-[[[5-(phenylmethoxy)pentyl]oxy]methyl]-

929619-00-1
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202577-32-0
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1-Pentanol, 5-(phenylmethoxy)-, 1-(4-methylbenzenesulfonate)

141177-22-2
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202577-32-0
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