1,3-Dihydro-3-oxo-1-isobenzofuranacetic acid → 2-(3-Phthalidyl)ethanol

HRID 970702Notes

Reaction equation

HRID 970702 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12](O)=[O:13])[O:3]1)=[O:2].CSC.B>C1COCC1>[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][CH2:12][OH:13])[O:3]1)=[O:2]

Participants

4

Reactant 2

HCID 5897301,3-Dihydro-3-oxo-1-isobenzofuranacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 222749702-(3-Phthalidyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phthalide-3-acetic acid (1 mmole) in THF was treated with borane dimethylsulfide (1.5 mmole) at 0° C. for 1 h, and at 25° C. for 24 h. Extraction and chromatography gave 2-(3-phthalidyl)ethanol as a light yellow oil: Rf=0.25, 50% EtOAc-hexane.

Workup

  1. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-39adde3dbd67406cad24141fbaad4d20
Source dataset
uspto-grants-2007_12
Patent number
US07312219B2

Reaction notes

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