Borane;tetrahydrofuran → HCID 21792247, compound

HRID 542079Notes

Reaction equation

HRID 542079 reaction equation
B.C1COCC1.[OH:7][CH2:8][CH:9]([C:14]([F:21])([N+:18]([O-:20])=[O:19])[N+:15]([O-:17])=[O:16])[CH2:10][C:11](O)=[O:12]>O>[F:21][C:14]([N+:18]([O-:20])=[O:19])([N+:15]([O-:17])=[O:16])[CH:9]([CH2:10][CH2:11][OH:12])[CH2:8][OH:7]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 20209243HCID 20209243, compound

Product 1

HCID 21792247HCID 21792247, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 1M solution of borane-THF (5 ml, 5 mmole) stirred under a nitrogen atmosphere in an ice bath was added 1.0 g (4.8 mmole) of 4-hydroxy-3-(fluorodinitromethyl)butyric acid, gamma-lactone. The solution was then held in a water bath at 25°-28° C. for 24 hr. before 1 ml of water was slowly added dropwise. The solution was poured into 15 ml of water and extracted with ether to give 1.02 g (100%) of an oil which was essentially pure by TLC. Chromatography on silica gel 60 using methylene chloride-acetone (80/20) as eluent gave an analytical sample. 1H NMR (CDCl3) 1.70-1.93 (m, 2H), 2.36(OH), 3.34-3.97 (m, 5H); IR (film) 3700-3050 (OH), 1605 (NO2) cm-1.

Workup

  1. extractionextracted with ether

Sources & evidence

ORD record
ord-67b238a42f3a4ceba3e844c91d53c9f7
Source dataset
uspto-grants-1987_04
Patent number
USH0000253

Reaction notes

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