Benzyl Bromide → Benzyl 2,3-dihydrofuran-3-carboxylate

HRID 1108494Notes

Reaction equation

HRID 1108494 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[O:1]1[CH:5]=[CH:4][CH:3]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:2]1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 102683-Furoic acid

Product 1

HCID 18785169Benzyl 2,3-dihydrofuran-3-carboxylate

Procedure

Synthesis takes place first of all by Birch reduction of 3-furancarboxylic acid followed by esterification with benzyl bromide to form benzyl 2,3-dihydrofuran-3-carboxylate (in accordance with G. Lowe, St. Swain; J. Chem. Soc. Perkin Trans I (1985), 391) ##STR29## b) The end product from a) is reduced with lithium aluminum hydride to give 3-hydroxymethyl-2,3-dihydrofuran

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-0b3b7cc51dd74bfab1171537632f93c7
Source dataset
uspto-grants-2000_05
Patent number
US06066746

Reaction notes

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