Tetrahydrofuran → HCID 21474711, compound

HRID 2294370Notes

Reaction equation

HRID 2294370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH2:13][CH2:14][CH2:15][C:16](OCC)=[O:17])[CH2:8]1.[BH4-].[Na+].O1CCCC1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH2:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21474799HCID 21474799, compound

Product 1

HCID 21474711HCID 21474711, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Preparation 5 was repeated, except that 1.43 g of ethyl 4-[5-(3-chlorophenoxymethyl)-2-oxooxazolidin-3-yl]butyrate (prepared as described in Preparation 116), 183 mg of sodium borohydride, 20 ml of anhydrous tetrahydrofuran and 135 mg of anhydrous methanol were used, to give 1.26 g of the title compound having an Rf value of 0.31 (on silica gel thin layer chromatography, using ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 5

Sources & evidence

ORD record
ord-bfa40e47ee2c4e6f8dfd667be26093dc
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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