Hydrochloric Acid → HCID 90281956, compound

HRID 1497531Notes

Reaction equation

HRID 1497531 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[C:11]([Cl:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+].Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[C:11]([Cl:20])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 90282105HCID 90282105, compound

Product 1

HCID 90281956HCID 90281956, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-(benzyloxy)-2-chlorophenyl]propanoic acid (1.00 g) in tetrahydrofuran (20.0 mL) was added 1,1′-carbonyldiimidazole (1.11 g), followed by stirring at room temperature for 2 hours. Subsequently, sodium borohydride (520 mg) and water (4.00 mL) were added thereto, followed by stirring at room temperature for 1 hour. To the reaction mixture was added 1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 3-[4-(benzyloxy)-2-chlorophenyl]propan-1-ol (861 mg).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9958e59cb3c74789a497523c090c1feb
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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