Hydrochloric Acid → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

HRID 2193130Notes

Reaction equation

HRID 2193130 reaction equation
[F:1][C:2]1([F:14])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11](O)=[O:12])=[CH:10][C:4]=2[O:3]1.ClC(OCC(C)C)=O.[BH4-].[Na+].Cl>C(N(CC)CC)C.O1CCCC1>[F:14][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62365Isobutyl chloroformateHCID 6087722,2-Difluoro-1,3-benzodioxole-5-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Into 50 mL of tetrahydrofuran, 962 mg of 2,2-difluorobenzo[1,3]dioxol-5-carboxylic acid was suspended, 0.8 mL of triethylamine was added to the suspension, and after cooling with ice, thereto was added 0.75 mL of isobutyl chloroformate. The mixture was stirred for 1 hour, and then 662 mg of sodium borohydride was added thereto, and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was acidified with 1 mol/L hydrochloric acid, the solvent was removed under reduced pressure, and ethyl acetate was added thereto. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 942 mg of a colorless oily substance, (2,2-difluorobenzo[1,3]dioxol-5-yl)methanol.

Workup

  1. temperatureafter cooling with ice
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. customthe solvent was removed under reduced pressure, and ethyl acetate
  4. additionwas added
  5. customThe organic layer was separated
  6. washwashed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ff0728d070404ffabb3b2162c33e3345
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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