Triethylamine → Benzyl [hydroxy-(4-phenylbutyl)phosphinyl] acetate
Reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][P:13]([CH2:25]C(O)=O)([CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:14].C(N(CC)CC)C.OS([O-])(=O)=O.[K+]>O1CCCC1.C(OCC)(=O)C>[OH:14][P:13]([CH2:25][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])([CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of benzyl chloroformate (1.8 ml, 12.6 mmol) in 5 ml of dry tetrahydrofuran was added dropwise to a solution of [hydroxy(4-phenylbutyl)phosphinyl]acetic acid (2.55 g, 10 mmol) and triethylamine (2.0 ml, 14.5 mmol) in 30 ml of dry tetrahydrofuran at 0° C. After addition was complete, the mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. The mixture was positioned between ethyl acetate and 5% KHSO4 and the ethyl acetate layer was evaporated to a residue. The residue was taken up in aqueous NaHCO3, washed with ethyl acetate, and the aqueous solution acidified to pH 1 and extracted with ethyl acetate. The extracts were dried (Na2SO4) and evaporated to give the crude product which was triturated with pentane to yield a solid, melting point 64°-67° C. (3.30 g).
Workup
- additionAfter addition
- customthe ethyl acetate layer was evaporated to a residue
- washwashed with ethyl acetate
- extractionextracted with ethyl acetate
- dry with materialThe extracts were dried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-1fe0bf697d084e55a0ff67ac6ef97a1e
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04396772
Reaction notes
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