Hydrochloric Acid → 4-(1-Hydroxy-4-iodobutyl)-alpha,alpha-dimethylphenylacetic acid

HRID 1294090Notes

Reaction equation

HRID 1294090 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[BH4-].[Na+].Cl>CO>[OH:6][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)[CH2:4][CH2:3][CH2:2][I:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 113143824-(4Iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetic acid

Product 1

HCID 222227064-(1-Hydroxy-4-iodobutyl)-alpha,alpha-dimethylphenylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 50 mg of 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetic acid, prepared in accordance with Example 3, in 3 mL of methanol was added 50 mg of NaBH4. The mixture was stirred for 30 minutes, acidified with 2N HCl, and the methanol-removed in vacuo. The concentrate was extracted with EtOAc. The organics were dried over Na2SO4, filtered, and concentrated to afford 40 mg of 4-(1-hydroxy-4-iodobutyl)-α,α-dimethylphenylacetic add.

Workup

  1. customthe methanol-removed in vacuo
  2. extractionThe concentrate was extracted with EtOAc
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 40 mg of 4-(1-hydroxy-4-iodobutyl)-α,α-dimethylphenylacetic
  7. additionadd

Sources & evidence

ORD record
ord-eb0778fdb48e42d0b7af6997ce57b228
Source dataset
uspto-grants-2007_07
Patent number
US07238834B2

Reaction notes

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