HCID 13311996, compound → HCID 22025284, compound

HRID 489223Notes

Reaction equation

HRID 489223 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[Br:15][C:12]1[CH:11]=[CH:10][C:9]([CH:7]([OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][OH:2])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 13311996HCID 13311996, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22025284HCID 22025284, compoundYield 80.6%

Procedure

Using the procedure described in Preparation 3, 5-(4-bromophenyl)-5-oxopentanoic acid methyl ester (12.8 g, 45 mmol) (Preparation 12) was reduced with LiAlH4 (3.4 g, 90 mmol) to yield 1-(4-bromophenyl)-pentane-1,5-diol (9.4 g) as a yellow oil. 1H NMR (CDCl3): 7.42 (2H, d, J=8.3 Hz), 7.15 (2H, d, J=8.3 Hz), 4.56 (1H, m), 3.63 (1H, br s), 3.45-3.6 (2H, m), 2.96 (1H, br s), 1.25-1.9 (6H, m).

Sources & evidence

ORD record
ord-1866673ecfc7402197d5fc8769f9d788
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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