Benzyl Alcohol → Benzyl tetrahydro-2H-pyran-4-carboxylate

HRID 16608

반응식

HRID 16608 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.O=S(Cl)Cl.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:8])[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 24386Thionyl ChlorideHCID 219302Oxane-4-carboxylic acid

생성물 1

HCID 23131611Benzyl tetrahydro-2H-pyran-4-carboxylate수율 70.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

A mixture of tetrahydropyran-4-yl-carboxylic acid (910 mg, 6.99 mmol) and SOCl2 (5.0 mL) was stirred for 1 h at 60° C. and concentrated in vacuo. To the residue were added benzyl alcohol (1.52 g, 14.1 mmol) and tetrahydrofuran (5.0 mL) at ambient temperature. The resulting mixture was stirred for 13 h at ambient temperature and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (silica gel, eluting with hexane/ethyl acetate (2:1)) to give 1.08 g (70%) of the title compound as a pale yellow oil.

후처리

  1. concentrationconcentrated in vacuo
  2. stirringThe resulting mixture was stirred for 13 h at ambient temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (silica gel, eluting with hexane/ethyl acetate (2:1))

출처 및 근거

ORD 기록
ord-8fd06a8b3539453b86ef5bd3c688a452
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737163B2

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