Acetic Acid → HCID 69516318, compound

HRID 854960Notes

Reaction equation

HRID 854960 reaction equation
[CH3:1][C:2]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]([C:16]([F:19])([F:18])[F:17])[O:13]2)=[CH:8][CH:7]=1)([CH3:5])[CH:3]=[O:4].[BH4-].[Na+].CC(O)=O>CO>[OH:4][CH2:3][C:2]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]([C:16]([F:18])([F:19])[F:17])[O:13]2)=[CH:8][CH:7]=1)([CH3:5])[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86599474HCID 86599474, compound

Product 1

HCID 69516318HCID 69516318, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 7-(1,1-dimethyl-2-oxoethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate (6.90 g, 20.2 mmoles) in 200 mL of MeOH stirring in an ice bath, was added portionwise NaBH4 (763 mg, 20.2 mmoles) as a solid. After 25 min, HOAc was cautiously added, and the solution concentrated. The residue was partitioned between DCM and water, and the organic extract dried over Na2SO4, filtered, and evaporated. Chromatography of the residue over silica gel using a gradient of 0-10% EtOAc—DCM as eluent gave the title compound, 5.4 g, as a very pale yellow oil.

Workup

  1. concentrationthe solution concentrated
  2. customThe residue was partitioned between DCM and water
  3. extractionthe organic extract
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-237672ec89964ca4b73960edfb1232a7
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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