Sodium hydride → Z-2-Acetoxy-2-acetyl-5,9-dimethyl-deca-4,8-dienoic acid, tert-butyl ester

HRID 130374Notes

Reaction equation

HRID 130374 reaction equation
[C:1]([O:4][CH:5]([C:13]([CH3:15])=[O:14])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[H-].[Na+].[H][H].[CH2:20](Br)/[CH:21]=[C:22](\[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])/[CH3:23]>C1COCC1>[C:1]([O:4][C:5]([C:13](=[O:14])[CH3:15])([CH2:20]/[CH:21]=[C:22](/[CH3:23])\[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:6]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 6087681Neryl bromideHCID 11736056Tert-butyl 2-acetoxyacetoacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 12046018Z-2-Acetoxy-2-acetyl-5,9-dimethyl-deca-4,8-dienoic acid, tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-butyl 2-acetoxyacetoacetate (B1) (19.5 g, 90 mmol) was added dropwise to a stirred suspension of NaH (2.59 g, 108 mmol) in THF (180 mL) at 0° C. After the liberation of hydrogen gas stopped, nerylbromide (19.6 g, 90 mmol) was added dropwise at 0° C. Afterwards the ice bath was removed and the mixture stirred at room temperature for 16 hours. The resulting mixture was diluted with ether (750 mL), washed with water (3 200 mL) and brine (1 200 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used without further purification.

Workup

  1. customAfterwards the ice bath was removed
  2. additionThe resulting mixture was diluted with ether (750 mL)
  3. washwashed with water (3 200 mL) and brine (1 200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-9db70e5d12a8424f9c947009fcdb7fda
Source dataset
uspto-grants-2008_06
Patent number
US07381743B2

Reaction notes

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