Triphenylphosphine → (R)-(-)-1-Methyheptyl 4-Methoxycarbonyloxybenzoate

HRID 433042노트

반응식

HRID 433042 반응식
[CH3:1][O:2][C:3]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:4].[CH3:15][C@H:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][C@H:16]([CH3:15])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:11])=[CH:8][CH:7]=1)=[O:4]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2723888(+)-2-OctanolHCID 222422684-[(Methoxycarbonyl)oxy]benzoic acid

생성물 1

HCID 70010659(R)-(-)-1-Methyheptyl 4-Methoxycarbonyloxybenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Compound 2 (15.0 g, 77 mmol), (S)-(+)-octan-2-ol (10.0 g, 77 mmol) and diethyl azodicarboxylate (3.4 g, 77 mmol) were dissolved in THF (250 ml) and triphenylphosphine (22.3 g, 85 mmol) in THF (50 ml) was added dropwise with stirring. The reaction mixture was left stirring under nitrogen until no further reaction was visible by TLC. The solvent was then removed in vacuo and the resulting slurry was purified by column chromatography [petroleum ether (bp 40-60° C.): dichloromethane (12:1)] on silica to yield a colourless oil.

후처리

  1. waitThe reaction mixture was left
  2. stirringstirring under nitrogen until no further reaction
  3. customThe solvent was then removed in vacuo
  4. customthe resulting slurry was purified by column chromatography [petroleum ether (bp 40-60° C.): dichloromethane (12:1)] on silica
  5. customto yield a colourless oil

출처 및 근거

ORD 기록
ord-3fcb648bddb14526a4c217beeff081cc
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06666989B1

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