tert-Butanol → 4-Pentynoic acid, 1,1-dimethylethyl ester

HRID 1482250

Reaction equation

HRID 1482250 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].[CH3:8][C:9](O)([CH3:11])[CH3:10].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:7][C:9]([CH3:11])([CH3:10])[CH3:8])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acid

Product 1

HCID 108773414-Pentynoic acid, 1,1-dimethylethyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Pent-4-ynoic acid (5.0 g, 51.0 mmol), 2-methylpropan-2-ol (7.56 g, 102.0 mmol) and 4-(dimethylamino)pyridine (0.31 g, 2.54 mmol) were dissolved in DCM (17.5 ml), a solution of dicyclohexylcarbodiimide (11.6 g, 56.2 mmol) in DCM (17.5 ml) was added and the mixture was stirred at room temperature overnight. The white solid in the reaction solution was removed by filtration, after which the filtrate was washed with a 0.5 M aqueous hydrochloric acid solution and a saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The residue obtained by filtration and concentration under reduced pressure was purified by silica gel column chromatography (DCM) to afford the title compound (Compound SP429) (7.15 g, 91.0%).

Workup

  1. customThe white solid in the reaction solution was removed by filtration
  2. washafter which the filtrate was washed with a 0.5 M aqueous hydrochloric acid solution
  3. dry with materiala saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate
  4. customThe residue obtained by filtration and concentration under reduced pressure
  5. customwas purified by silica gel column chromatography (DCM)

Sources & evidence

ORD record
ord-5af35e94f05a440e8c6be544e402046b
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Linked notes

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