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

HRID 433042Notes

Reaction equation

HRID 433042 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3fcb648bddb14526a4c217beeff081cc
Source dataset
uspto-grants-2003_12
Patent number
US06666989B1

Reaction notes

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