Potassium sodium tartarate → HCID 57989006, compound

HRID 471328Notes

Reaction equation

HRID 471328 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10](OCC)=[O:11].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][CH2:10][OH:11]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 57989229HCID 57989229, compound

Product 1

HCID 57989006HCID 57989006, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 9-bromo-4,4-dimethylnonanoate (example 285, step g) (0.56 g) in dry ether (19 mL) under nitrogen at 0° C. was treated with diisobutylaluminium hydride (1M in toluene, 4.20 mL) and the reaction mixture was stirred at 0° C. for 1 hour 15 minutes. The reaction mixture was treated cautiously with aqueous potassium sodium tartrate solution and stirred for 1 hour. The phases were separated and the aqueous layer was extracted with ether (×2) then the combined organic phase was washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the subtitled compound as a colourless oil. Yield 0.42 g.

Workup

  1. stirringstirred for 1 hour
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with ether (×2)
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d9171260f7914e099f454f6b254e6ce0
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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