Diketene → HCID 87384784, compound

HRID 1055230Notes

Reaction equation

HRID 1055230 reaction equation
[NH2:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5].[CH2:8]=[C:9]1[O:13][C:11](=[O:12])[CH2:10]1>O1CCCC1>[OH:5][CH2:4][C:3]([CH3:7])([CH3:6])[CH2:2][NH:1][C:11](=[O:12])[CH2:10][C:9](=[O:13])[CH3:8]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 1173261-Propanol, 3-amino-2,2-dimethyl-

Product 1

HCID 87384784HCID 87384784, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 32.2 g (0.31 mol) of 3-amino-2,2-dimethyl-propan-1-ol in 60 ml tetrahydrofuran was added dropwise to a solution of 25 g of diketene (0.30 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue is recrystallized from 150 ml of ethyl acetate. This gave 40.6 g (0.21 mol, 73% yield) of a colorless solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue is recrystallized from 150 ml of ethyl acetate

Sources & evidence

ORD record
ord-b265e0a3c7d243359b51033168ff130e
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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