Sodium Hydroxide → 2,2-Dimethylhept-4-yn-1-ol

HRID 1360643Notes

Reaction equation

HRID 1360643 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([CH3:19])([CH2:14][C:15]#[C:16][CH2:17][CH3:18])[C:9](OCC)=[O:10].[OH-].[Na+]>CCOCC>[CH3:7][C:8]([CH3:19])([CH2:14][C:15]#[C:16][CH2:17][CH3:18])[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14410114Ethyl 2,2-dimethylhept-4-ynoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 578554552,2-Dimethylhept-4-yn-1-olYield 89.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a slurry of LiAlH4 (7.4 g, 194 mmol) in anhydrous Et2O (200 ml) at 0° C. was added a solution of ethyl 2,2-dimethylhept-4-ynoate (29 g, 159 mmol) in anhydrous Et2O (100 ml) slowly over a period of 30 min. The reaction mixture was stirred at 0° C. for 3 hours. A 10% aqueous solution of NaOH (35 ml) was added slowly. The solid was filtered off. The filtrate was washed with brine, dried (MgSO4) and the solvent was removed under reduced pressure to afford the titled compound as a colorless liquid (20 g, 89%). TLC: Pet. ether/EtOAc (8/2): Rf=0.3. 1H NMR (CDCl3, 300 MHz) δ 0.95 (6H, s), 1.03 (3H, t), 1.81 (1H, br. s), 2.10 (2H, s), 2.17 (2H, m), 3.14 (2H, s).

Workup

  1. filtrationThe solid was filtered off
  2. washThe filtrate was washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6ec2297f808445db99dba18a149d82a7
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

Loading…