tert-Butanol → HCID 69992339, compound

HRID 1250119Notes

Reaction equation

HRID 1250119 reaction equation
[Li+].CCC[CH2-].[CH3:6][C:7]([OH:10])([CH3:9])[CH3:8].C[O:12][C:13](=O)[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[C:7]([O:10][C:13](=[O:12])[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1)([CH3:9])([CH3:8])[CH3:6]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 25517Ammonium ChlorideHCID 61028n-Butyl lithiumHCID 69991466HCID 69991466, compound

Product 1

HCID 69992339HCID 69992339, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Butyllithium (4.43 mL, 11.07 mmol) was added to a solution 2-methyl-2-propanol (1.0 mL, 10.53 mmol) in tetrahydrofuran (21 mL) at −10° C. under an argon atmosphere, and the mixture was stirred for 10 minutes. A solution of 4-(3-bromophenyl)butyric acid methyl ester (1.35 g, 5.27 mmol) in tetrahydrofuran (5.3 mL) was added dropwise at −10° C., and the mixture allowed to reach room temperature and stirred for 16 hours. Saturated ammonium chloride was added and the product extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate (98:2), gave 4-(3-bromophenyl)butyric acid tert-butyl ester as a yellow oil (74%).

Workup

  1. customto reach room temperature
  2. stirringstirred for 16 hours
  3. extractionthe product extracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography
  7. washeluting with hexane/ethyl acetate (98:2)

Sources & evidence

ORD record
ord-30a6777f48ff4651b6d994b2dfbe23b3
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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