Benzenepentanol, α-[2-(4-hydroxy-3-methoxyphenyl)ethyl]- synthesis
- Product Name:Benzenepentanol, α-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-
- CAS Number:87657-77-0
- Molecular formula:C20H26O3
- Molecular Weight:314.43
78954-23-1
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Yield:87657-77-0 87%
Reaction Conditions:
with sodium tetrahydroborate in methanol at 0 - 20; for 2 h;
Steps:
Oxyphyllacinol (1)
A solution of 11 (40 g, 0.13 mol, 1.0 equiv) in MeOH was added NaBH4 (10 g, 0.26 mol,2.0 equiv) portion-wise at 0 C. Then the reaction temperature was heated to room temperaturealong with being stirred for 2 h. After completion of the reaction (monitoredby TLC), excess NaBH4 was quenched with water and the solvent was removed underreduced pressure. EtOAc and water were added to the residue. The organic layer wasseparated, washed with brine, dried over anhydrous Na2SO4, filtered, and concentratedunder reduced pressure. The crude product was purified by recrystallization (Hexane/petroleum ether, 1:5, 10 C) to afford oxyphyllacinol (1) (71 g, 87%) as white waxysolid at 0 C.1H NMR (500 MHz, CDCl3) d 7.24 (d, J7.9 Hz, 2H, Ar-H), 7.14 (d,Scheme 6. Synthesis of yakuchinone-B (13).6 X. SHI ET AL.J7.9 Hz, 3H, Ar-H), 6.81 (d, J7.8 Hz, 1H, Ar-H), 6.67 (s, 1H, A-H), 6.66 (d,J7.8 Hz, 1H, Ar-H), 3.85 (s, 3H, OCH3), 3.63-3.57 (m, 1H, CHOH), 2.66-2.72 (m,1H, ArCH2CH2CHOH), 2.59 (t, J7.5 Hz, 2H, CH2), 2.58-2.54 (m, 1H,ArCH2CH2CHOH), 1.76-1.65 (m, 2H, CH2), 1.64-1.53 (m, 2H, CH2), 1.54-1.41 (m,3H, CH2 and CH2CH2CHOH), 1.39-1.33 (m, 1H, CH2CH2CHOH); 13C NMR(125 MHz, CDCl3) d 146.44, 143.74, 142.52, 134.05, 128.37, 128.27, 125.67, 120.91,114.29, 111.03, 71.30, 55.88, 39.35, 37.45, 35.88, 31.75, 31.44, 25.26; HR-MS (ESI) calcdfor C20H25O3 [M-H]- 313.4250, found 313.4226. All the above data are consistent withthose in the reported literature.[18]
References:
Shi, Xiang;Deng, Yu;Kurtz, Nicole C.;Sun, Yue;Xue, Mingxing;Wu, Xian [Synthetic Communications,2022,vol. 52,# 4,p. 513 - 520]
14171-89-2
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3360-41-6
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