Water → 3,5-dibenzyloxyphenol

HRID 217542노트

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HRID 217542 반응식
C(S)C.[H-].[Na+].[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20]CC2C=CC=CC=2)[CH:17]=[C:16]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>CN(C=O)C>[CH2:29]([O:28][C:16]1[CH:17]=[C:18]([OH:20])[CH:19]=[C:14]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:15]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 10916273Benzene, 1,3,5-tris(phenylmethoxy)-

생성물 1

HCID 118229213,5-dibenzyloxyphenol수율 11%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

Ethanethiol (10 g, 216 mmol) was added dropwise to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 2.4 g, 100 mmol) in dry DMF (120 mL) at 0° C. After 1 h, 1,3,5-tribenzyloxybezene (24 g, 60 mmol) was added in 10 batches and the mixture was heated to 150° C. for 1.5 h. After the reaction was cooled, water (500 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (benzene) to give 3,5-dibenzyloxyphenol as white solid (11%) after recrystallization from carbon tetrachloride and product #d as white solid (56%) after recrystallization from EtOAc and hexane. Compound #d was identified by mp 107-109° C.; 1H NMR (CDCl3, 400 MHz) δ 7.36-7.23 (m, 15H), 6.25 (d, J=2.2 Hz, 1H), 6.07 (d, J=2.2 Hz, 1H), 4.96 (s, 2H), 4.92 (s, 2 H), 3.99 (s, 2H); 13C NMR (CDCl3, 400 MHz) δ 158.4, 157.9, 154.9, 140.7, 136.7, 136.6, 128.4, 128.2, 128.1, 127.8, 127.5, 127.3, 127.0, 125.6, 108.5, 94.7, 93.3, 70.2, 69.9, 28.3; HRMS (ESI) calcd for C27H24O3Na (M+Na) 419.1623. found 419.1645.

후처리

  1. temperatureAfter the reaction was cooled
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel (benzene)

출처 및 근거

ORD 기록
ord-5e7b1fa9df95497580ac703054e9265b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193377B2

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