Triphenylphosphine → HCID 14574967, compound

HRID 231248Notes

Reaction equation

HRID 231248 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[CH2:10][C:11]1([O:19][CH2:18][CH2:17][O:16]1)[CH2:12][C:13](O)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1.CC(C)=O.[BH4-].[Cu+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:18]1[CH2:17][O:16][C:11]([CH2:12][CH:13]=[O:14])([CH2:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:20])[O:19]1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 65578Oxalyl chlorideHCID 14574965HCID 14574965, compound

Product 1

HCID 14574967HCID 14574967, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 12406461Borate(1-), tetrahydro-, bis(triphenylphosphine)copper(1+)CatalystHCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

By following the procedure employed in Preparation 1, E. and F., 3,3-(ethylenedioxy)glutaric acid mono benzyl ester prepared as described above in step A. (2.937 g, 10.48 mmole) was converted to the corresponding acid chloride with oxalyl chloride (3.0 ml, 34.39 mmole) in 30 ml of benzene. The acid chloride was reduced with bis(triphenylphosphine) copper (I) tetrahydroborate (6.32 g, 10.48 mmole) and triphenylphosphine (5.5 g, 20.97 mmole) in 50 ml of acetone. There was obtained 1.930 g, 70% yield of benzyl 3,3-(ethylenedioxy)-4-formylbutyrate, as a colorless syrup.

Workup

  1. customemployed in Preparation 1, E

Sources & evidence

ORD record
ord-0bbbe448de364fd29ce0efb68ca31384
Source dataset
uspto-grants-1989_07
Patent number
US04845229

Reaction notes

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