1-Bromooctane → HCID 57091148, compound

HRID 863177Notes

Reaction equation

HRID 863177 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([O:16][CH3:17])[C:14]([CH3:19])([CH3:18])[CH2:13][CH2:12][C@H:11]1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C=O>[CH3:17][O:16][C@H:15]1[C:14]([CH3:18])([CH3:19])[CH2:13][CH2:12][C@@H:11]([O:20][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C@H:10]1[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 53912347HCID 53912347, compound

Product 1

HCID 57091148HCID 57091148, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (1R,2R,3R)-2-(benzyloxymethyl)-3-methoxy-4,4-dimethylcyclohexanol (7 mg) and sodium hydride (5 mg, 60% dispersion in oil) and n-octyl bromide (20 ml) in dry N,N-dimethylformamide (0.3 ml) was stirred for 2 hrs at room temperature. The mixture was cooled to 0° C., and the reaction was quenched by addition of water. The pH of the mixture was adjusted to pH 7 with 0.1N hydrochloric acid. The mixture was extracted with diethyl ether, and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the residue by preparative thin layer chromatography (using n-hexane:ethyl acetate=10:1 as an eluent) gave benzyl [(1R,2R,6R)-2-methoxy-3,3-dimethyl-6-octyloxycyclohexyl]methyl ether (8 mg, 83%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe reaction was quenched by addition of water
  3. extractionThe mixture was extracted with diethyl ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-20223d03080145b2981cc16eaec5ce9f
Source dataset
uspto-grants-1998_02
Patent number
US05719291

Reaction notes

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