Dichloromethane → Methyl 2-methanesulfonyloxy-3-phenyl-propionate

HRID 1613899노트

반응식

HRID 1613899 반응식
ClCCl.[OH:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl.CCOCC>[CH3:24][S:25]([O:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:27])=[O:26]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 518800Methyl 2-hydroxy-3-phenylpropanoate

생성물 1

HCID 13662406Methyl 2-methanesulfonyloxy-3-phenyl-propionate수율 93%

시약·촉매·용매 1

HCID 21881112Ethyl ether methylene chloride용매

실험 절차

A dichloromethane solution of methyl 2-hydroxy-3-phenylpropionate (33) is treated with triethylamine (1.1 equiv) and methanesulfonyl chloride (1.1 equiv) at 0° C. Upon completion of reaction, the mixture is dissolved in dichloromethane/ether and washed with saturated aqueous solution of sodium chloride, dried and concentrated. Purification of crude material by flash column chromatography (40% ethyl acetate in hexane) gives methyl 2-methanesulfonyloxy-3-phenylpropionate (1.6 g, 93%). 1H NMR (300 MHz CDCl3): δ 7.358-7.233 (m, 5H), 5.173 (dd, 4.26 Hz, 8.8 Hz, 1H), 3.793 (s, 3H), 3.301 (dd, 4.23 Hz, 14.38 Hz, 1H), 3.1295 (dd, 8.8 Hz, 14.3 Hz, 1H), 2.766 (s, 3H).

후처리

  1. customUpon completion of reaction
  2. washwashed with saturated aqueous solution of sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customPurification of crude material by flash column chromatography (40% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-19bd6031de0f4784b9594288ab4a0b5a
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05194605

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