Hydrochloric Acid → HCID 178520929, compound

HRID 1406832Notes

Reaction equation

HRID 1406832 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C1COCC1.[BH4-].[Na+].Cl>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:10][CH2:11][C@H:12]([CH2:15][OH:16])[CH2:13][CH2:14]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 178520928HCID 178520928, compound

Product 1

HCID 178520929HCID 178520929, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Then, trans-4-(3,5-difluorophenyl)cyclohexane carbaldehyde (112 g) was dissolved in ethanol (224 mL), THF (30 mL), and water (30 mL), and sodium tetrahydroborate (9.4 g) was slowly added to the resultant solution at an outside temperature or 5° C., followed by stirring at an outside temperature of 5° C. for 10 minutes. The reaction solution was slowly poured into 10% hydrochloric acid (450 mL) and stirred for a white, and then an organic layer was separated. An aqueous layer was subjected to extraction with ethyl acetate, and the ethyl acetate extract was combined with the organic layer and washed with saturated brine two times. The mixture was dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to yield 110 g of trans-4-(3,5-difluorophenyl)cyclohexylmethanol as light yellow oil.

Workup

  1. stirringstirred for a white, and then an organic layer
  2. customwas separated
  3. extractionAn aqueous layer was subjected to extraction with ethyl acetate
  4. extractionthe ethyl acetate extract
  5. washwashed with saturated brine two times
  6. dry with materialThe mixture was dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0a4a11fac3064a18a8805862b4c684b1
Source dataset
uspto-grants-2014_12
Patent number
US08916718B2

Reaction notes

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