Acetic Anhydride → Acetic acid 5-benzyloxy-2-iodo-benzyl ester

HRID 132165

반응식

HRID 132165 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([I:17])=[C:13]([CH:16]=1)[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([I:17])=[C:13]([CH:16]=1)[CH2:14][O:15][C:18](=[O:20])[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 67318946(5-(Benzyloxy)-2-iodophenyl)methanol

생성물 1

HCID 59731894Acetic acid 5-benzyloxy-2-iodo-benzyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a well stirred solution of 3-benzyloxybenzyl alcohol (5.5 g, 25.7 mmol) in methanol (100 mL) and sodium hydrogencarbonate (8.4 g, 100 mmol) was added a 1.0 M solution of iodine monochloride in dichloromathane (30 mL) at 0° C. The reaction mixture was brought to room temperature and stirring continued for additional 1 h. The reaction mixture was concentrated and then diluted with dicholomethane (150 mL), washed with 10% aqueous sodium thiosulfate and dried (Na2SO4). The desired compound was purified by flash chromatography (silica) using 20% ethyl acetate in hexane to give 5-benzyloxy-2-iodobenzyl alcohol (6.2 g, 71% yield). The alcohol (4.2 g, 12.4 mmol) was dissolved in dichloromethane (100 mL) added acetic anhydride (2.52 g, 24.7 mmol) and catalytic amount of 4-dimethylaminopyridine. The reaction mixture was then stirred for 12 h, washed with aqueous sodium hydrogencarbonate and then dried (Na2SO4) to give acetic acid 5-benzyloxy-2-iodo-benzyl ester in quantitative yield. MS (ESI) 405 (M+Na); Rf=2.27.

후처리

  1. washwashed with aqueous sodium hydrogencarbonate
  2. dry with materialdried (Na2SO4)

출처 및 근거

ORD 기록
ord-2b03ba3cf0404575998afe96718b8989
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384930B2

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