Benzyl mercaptan → 3-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid ethyl ester

HRID 1796140ノート

反応式

HRID 1796140 の反応式
[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[CH2:6])[CH3:2].C([O-])(O)=O.[Na+].[CH2:21]([SH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C.O>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:6][S:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:2]

参加物

6

反応物 3

HCID 7509Benzyl mercaptanHCID 516892Sodium BicarbonateHCID 210257162-(Tetrahydro-pyran-4-yloxymethyl)-acrylic acid ethyl ester

生成物 1

HCID 694384543-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid ethyl ester収率 36.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A suspension of 2-(tetrahydro-pyran-4-yloxymethyl)-acrylic acid ethyl ester (2.2 g, 10.2 mmol) in ethanol (100 ml) was treated with a solution of NaHCO3 (0.86 g, 10.2 mmol) in water ml (10 ml) and benzyl mercaptan (1.21 ml, 10.2 mmol) at room temperature overnight. Ethanol evaporated off under reduced pressure, crude partitioned between ethyl acetate and water, organic layer separated and purified by mplc eluting with 1:9 to 2:8 v/v ethyl acetate-heptane mixture to give the title compound as pale yellow oil (1.27 g). MS: 339 (MH+); LCMS (Protocol B) retention time 4.3 minutes.

後処理

  1. customEthanol evaporated off under reduced pressure, crude
  2. custompartitioned between ethyl acetate and water, organic layer
  3. customseparated
  4. custompurified
  5. washby mplc eluting with 1:9 to 2:8 v/v ethyl acetate-heptane mixture

出典と根拠

ORDレコード
ord-d8812ce882d7483cbcd6dbb7c2a19dc8
出典データセット
uspto-grants-2006_04
特許番号
US07030116B2

反応ノート

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