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

HRID 1796140노트

반응식

HRID 1796140 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d8812ce882d7483cbcd6dbb7c2a19dc8
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030116B2

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