Hydrochloric Acid → HCID 178520605, compound

HRID 726508Notes

Reaction equation

HRID 726508 reaction equation
[BH4-].[Li+].O1CCCC1.Cl.[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][CH2:25][CH2:26][C:27](OCC)=[O:28])[CH2:19][CH2:18]1>>[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C@H:17]1[CH2:18][CH2:19][C@H:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH2:21][CH2:22]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 4148881Lithium borohydrideHCID 178471410HCID 178471410, compound

Product 1

HCID 178520605HCID 178520605, compoundYield 71.2%

Procedure

First, 1.3 g of lithium borohydride and 45 ml of dry tetrahydrofuran were placed in a 200 ml flask. Then, 30 ml of a tetrahydrofuran solution in which 7.7 g of 2,3-difluoro-1-[trans-4-(4-ethoxycarbonylbutyl)cyclohexyl]benzene was dissolved was added dropwise to the mixture, and the resultant mixture was stirred under reflux for 1 hour. Cold diluted hydrochloric acid was added to the reaction mixture, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1) and recrystallized from hexane to obtain 4.77 g of 2,3-difluoro-1-[trans-4-(5-hydroxypentyl)cyclohexyl]benzene (Y: 71.2%). The compound thus obtained had a purity of 98.9% by GC and 98.5% by HPLC.

Workup

  1. additionwas added dropwise to the mixture
  2. temperatureunder reflux for 1 hour
  3. extractionan organic layer was extracted with ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThereafter, the solvent was distilled away
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1)
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-f467a63beea24ac883f75c5704691ca8
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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