Borane → HCID 14742765, compound

HRID 1651241Notes

Reaction equation

HRID 1651241 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:17](O)=[O:18])[CH2:2][CH2:3][CH3:4].B>O1CCCC1>[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:17][OH:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6331BoraneHCID 14742763HCID 14742763, compound

Product 1

HCID 14742765HCID 14742765, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

As in Example 135, 1-butyl-7-methoxy-2-naphthalenecarboxylic acid (2.73 g) in tetrahydrofuran (15 ml) was treated with a solution of borane in tetrahydrofuran (1M; 22 mL) at 0°-5° C. and then mixture was stirred at room temperature overnight. The product was isolated in the usual manner and was crystallized from hexane to give 2.32 g of 1-butyl-7-methoxy-2-naphthalenemethanol, mp 52°-53° C. Anal. Calcd for C16H20O2 : C, 78.65; H, 8.25 Found: C, 78.50; H, 8.12

Workup

  1. customThe product was isolated in the usual manner
  2. customwas crystallized from hexane

Sources & evidence

ORD record
ord-df25bdbd6333469d8163c7d095106abc
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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