tert-Butanol → 1,1-Dimethylethyl 5-hexynoate

HRID 1482245Notes

Reaction equation

HRID 1482245 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[CH3:9][C:10](O)([CH3:12])[CH3:11].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:8][C:10]([CH3:12])([CH3:11])[CH3:9])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 1430365-Hexynoic acid

Product 1

HCID 109649121,1-Dimethylethyl 5-hexynoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Hex-5-ynoic acid (Compound SP424) (8.0 g, 71.3 mmol), 2-methylpropan-2-ol (10.6 g, 143.0 mmol) and 4-(dimethylamino)pyridine (0.44 g, 3.60 mmol) were dissolved in DCM (17.5 ml), a solution of dicyclohexylcarbodiimide (16.2 g, 78.5 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 column chromatography (hexane:ethyl acetate=100:0-90:10) to afford the title compound SP423 (6.73 g, 56.1%).

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 column chromatography (hexane:ethyl acetate=100:0-90:10)

Sources & evidence

ORD record
ord-09e679b9a2f641d6ab10361c5883f851
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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