Sodium hydride → HCID 11833521, compound

HRID 1087295Notes

Reaction equation

HRID 1087295 reaction equation
Cl[CH2:2][C@@:3]([CH3:7])([OH:6])[CH2:4][OH:5].[H-].[Na+].[CH3:10][CH:11]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:12][CH2:13][Mg]Br>O>[CH3:7][C@@:3]([OH:6])([CH2:2][CH2:13][CH2:12][CH:11]([CH3:10])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10866331HCID 10866331, compoundHCID 178443132HCID 178443132, compound

Product 1

HCID 11833521HCID 11833521, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

367 mg (3 mmol) of (2S)-3-chloro-2-methyl-1,2-propanediol were dissolved in 5 ml of dry tetrayhydrofuran and left to react at room temperature with 100 mg (7.2 mmol) of sodium hydride (55-60%) until the evolution of gas had finished. 350 mg of potassium tert.-butylate were added to the resulting thick suspension. Thereupon, 2.9 mmol of (3RS,7RS)-3,7,11-trimethyldodecylmagnesium bromide were added and the mixture was stirred at room temperature for 16 hours. 50 ml of water were subsequently added and the mixture was extracted with ether. The organic phases were dried over sodium sulphate and concentrated. There was obtained 0.81 g (96%) of (2R,6RS,10RS)-2,6,10,14-tetramethyl-1,2-pentadecanediol with [α]D20 =+1.35° (c=1.5% in CHCl3).

Workup

  1. waitleft
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe organic phases were dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8dd48b89336042b9b18b874253895199
Source dataset
uspto-grants-1991_07
Patent number
US05034546

Reaction notes

Loading…