Diethyl Ether → 3-(S)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanol

HRID 35720Notes

Reaction equation

HRID 35720 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C@H:13]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:14][C:15](OC)=[O:16].[OH-].[Na+]>O>[CH3:12][C@H:13]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:26])([CH3:28])[CH3:27])([CH3:23])[CH3:24])[CH2:14][CH2:15][OH:16]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 14234521HCID 14234521, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 100826933-(S)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To 8.5 g. (0.224 m) of lithium aluminum hydride in 250 ml. of diethyl ether under nitrogen was added 53.5 g. (0.206 m) of methyl 3-(R)-methyl-5-(t-butyldimethylsilyloxy)pentanoate in 125 ml. of ether. The reaction was stirred for one hour at 0° C. and was then treated dropwise with 8.4 g. of water, 8.4 ml. of a 15% sodium hydroxide solution and 25.2 ml. of water. The solids were filtered and the organic phase separated and washed with water, 2.5% hydrochloric acid and a brine solution. The organic phase was dried over magnesium sulfate and concentrated in vacuo to give 46 g. of product.

Workup

  1. additionwas then treated dropwise with 8.4 g
  2. filtrationThe solids were filtered
  3. customthe organic phase separated
  4. washwashed with water, 2.5% hydrochloric acid
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give 46 g

Sources & evidence

ORD record
ord-04c59c1a2f5f450fb1029576dc1a8df5
Source dataset
uspto-grants-1988_08
Patent number
US04767743

Reaction notes

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