Lithium borohydride → (3-Benzyloxy-4-iodophenyl)methanol

HRID 250842Notes

Reaction equation

[BH4-].[Li+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[I:21])[C:14](OC)=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.[Cl-].[NH4+]>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH2:14][OH:15])[CH:18]=[CH:19][C:20]=1[I:21])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.18 g (54 mmol, 3 eq) of lithium borohydride are added to a solution of 6.9 g crude (17.98 mmol, 1 eq) of methyl 3-benzyloxy-4-iodobenzoate in 30 ml of THF. The reaction mixture is heated at 60° C. for 12 hours and then hydrolyzed in saturated ammonium chloride solution NH4Cl and extracted with ethyl acetate. 6.5 g of (3-benzyloxy-4-iodophenyl)methanol are obtained in oil form and are used in the following reaction without further purification.

Workup

extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-2a15595a5b37457e9be50890b3622ef7
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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