Water → 4-Pentynoic acid, 1,1-dimethylethyl ester

HRID 2078006Notes

Reaction equation

HRID 2078006 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7](Br)([CH3:10])([CH3:9])[CH3:8].[C:12]([OH:18])(=[O:17])[CH2:13][CH2:14][C:15]#[CH:16].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CN(C)C(=O)C>[C:12]([O:18][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:17])[CH2:13][CH2:14][C:15]#[CH:16]

Participants

7

Reactant 4

HCID 962WaterHCID 10485t-Butyl bromideHCID 11430Potassium CarbonateHCID 224644-Pentynoic acid

Product 1

HCID 108773414-Pentynoic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
55 °C

Procedure

Benzyltriethylammonium chloride (5.92 g), potassium carbonate (93.4 g), and t-butyl bromide (143 ml) were added to a solution of 4-pentynoic acid (2550 mg) in N,N-dimethylacetamide (230 ml), and this reaction mixture was stirred at 55° C. for 24 hours. After water was added, the reaction mixture was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium chloride, and then filtered through silica gel. The filtrate was concentrated under reduced pressure to give the title compound (2.10 g). This compound was used in the following reaction without further purification.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium chloride
  4. filtrationfiltered through silica gel
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e1ea48393e741e0b320e147291cdfa7
Source dataset
uspto-grants-2011_04
Patent number
US07928209B2

Reaction notes

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