Borane → HCID 14742764, compound

HRID 1651236Notes

Reaction equation

HRID 1651236 reaction equation
B.[CH2:2]([C:6]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[C:18](O)=[O:19])[CH2:3][CH2:4][CH3:5]>O1CCCC1>[CH2:2]([C:6]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH2:18][OH:19])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 14742762HCID 14742762, compound

Product 1

HCID 14742764HCID 14742764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in tetrahydrofuran (1M; 10 mL) was added to a solution of 1-butyl-5-methoxy-2-naphthalenecarboxylic acid in tetrahydrofuran (15 mL) at 0°-5° C. and the mixture was stirred at room temperature for 3 hours. After the solvent was evaporated off, the reaction was diluted with 1N sodium hydroxide and extracted with dichloromethane. The organic layer was washed with brine then was dried (MgSO4), evaporated and crystallized from hexane to give 1.58 g of 1-butyl-5-methoxy-2-naphthalenemethanol, mp 100°-102° C. Recrystallization of a portion from diethyl ether-hexane afforded the pure alcohol, 101°-102° C. Anal. Calcd for C16H20O2 : C, 78.65; H, 8.25 Found: C, 78.36; H, 8.33

Workup

  1. customAfter the solvent was evaporated off
  2. additionthe reaction was diluted with 1N sodium hydroxide
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialthen was dried (MgSO4)
  6. customevaporated
  7. customcrystallized from hexane

Sources & evidence

ORD record
ord-2d7f5fd0c1e549f98f78455252745e59
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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