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

HRID 433042ノート

反応式

HRID 433042 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3fcb648bddb14526a4c217beeff081cc
出典データセット
uspto-grants-2003_12
特許番号
US06666989B1

反応ノート

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