Ammonia → 5-(2',2'-Dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol

HRID 1196175

Reaction equation

HRID 1196175 reaction equation
N.Br[C:3]1(Br)[C:5]([CH3:7])([CH3:6])[CH:4]1[CH2:8][CH2:9][C:10]([CH3:14])([OH:13])[C:11]#[CH:12].[Na]>C(OCC)C>[CH3:6][C:5]1([CH3:7])[CH2:3][CH:4]1[CH2:8][CH2:9][C:10]([CH3:14])([OH:13])[C:11]#[CH:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 538034755-(2'2'-Dibromo-3'3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol

Product 1

HCID 541287215-(2',2'-Dimethylcyclopropyl)-3-methyl-1-pentyn-3-olYield 48.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ammonia (54.5 ml) is placed in a reaction flask. A solution of 109.5 g (0.338 mol) of 5-(2',2'-dibromo-3',3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol dissolved in 415 ml of diethyl ether is added. Sodium (37.4 g, 1.662 mol) in small portions is added at -42° to -36° within 11/2 hours. The mixture is stirred for 13/4 h, the ammonia is evaporated and 830 ml of hexane are added dropwise. The mixture is then stirred for 30 minutes and 60 ml of ethanol are added dropwise. The mixture is then poured into a mixture of ice and acetic acid, extracted with ether, washed neutral and evaporated. The crude product (52.9 g) is distilled at 0.06 Torr. In this manner there are obtained 27.4 g (48%) of 5-(2',2'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol (purity 75%).

Workup

  1. additionis added
  2. customthe ammonia is evaporated
  3. addition830 ml of hexane are added dropwise
  4. stirringThe mixture is then stirred for 30 minutes
  5. addition60 ml of ethanol are added dropwise
  6. additionThe mixture is then poured into a mixture of ice and acetic acid
  7. extractionextracted with ether
  8. washwashed neutral
  9. customevaporated
  10. distillationThe crude product (52.9 g) is distilled at 0.06 Torr

Sources & evidence

ORD record
ord-a1a33a5e3887437095e884fdf64adfa9
Source dataset
uspto-grants-1992_05
Patent number
US05113021

Linked notes

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