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

HRID 1613899ノート

反応式

HRID 1613899 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 13662406Methyl 2-methanesulfonyloxy-3-phenyl-propionate収率 93%

試薬・触媒・溶媒 1

HCID 21881112Ethyl ether methylene chloride溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-19bd6031de0f4784b9594288ab4a0b5a
出典データセット
uspto-grants-1993_03
特許番号
US05194605

反応ノート

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