Hydrochloric Acid → HCID 178520636, compound

HRID 726496Notes

Reaction equation

HRID 726496 reaction equation
[BH4-].[Li+].O1CCCC1.Cl.C[O:10][C:11]([CH2:13][CH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[CH2:17][CH2:16]1)=O>>[OH:10][CH2:11][CH2:13][CH2:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[CH2:19][CH2:20]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 4148881Lithium borohydrideHCID 178500453HCID 178500453, compound

Product 1

HCID 178520636HCID 178520636, compoundYield 85.3%

Procedure

First, 1.4 g of lithium borohydride and 50 ml of dry tetrahydrofuran were placed in a 200 ml flask whose content was replaced with argon. Then, 25 ml of a tetrahydrofuran solution in which 12.1 g of 1-[trans-4-(2-methoxycarbonylethyl)cyclohexyl]-2,3-difluorobenzene was dissolved was added dropwise to the reaction mixture at room temperature, and the resultant reaction mixture was stirred under reflux for 1 hour. 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 9.3 g of 1-[trans-4-(3-hydroxypropyl)cyclohexyl]-2,3-difluorobenzene (Y: 85.1%). The compound thus obtained had a purity of 99.1% by GC and 99.0% by HPLC.

Workup

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

Sources & evidence

ORD record
ord-e590a6db37db4f959922666a64dd1f9e
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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