HCID 10997724, compound → HCID 59875688, compound

HRID 1700963Notes

Reaction equation

HRID 1700963 reaction equation
[CH3:1][C:2]([CH3:13])(/[C:8](/[CH2:11][CH3:12])=[CH:9]/[CH3:10])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]([CH3:13])(/[C:8](/[CH2:11][CH3:12])=[CH:9]/[CH3:10])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 10997724HCID 10997724, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 59875688HCID 59875688, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (E)-2,2-dimethyl-3-ethyl-3-pentenoate 23 (35.58 g, 193 mmol) is added dropwise to a suspension of lithium aluminium hydride (12.1 g, 320 mmol) in 81 ml of THF. The mixture is refluxed for 3 h, stirred for 16 h at r.t. and quenched with ice. The precipitate is filtered off by suction, washed several times with diethyl ether and hydrolyzed with 1 M hydrochloric acid. The aqueous solution is extracted with diethyl ether (3×100 ml). The combined etheral extracts are dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by vacuum distillation affords the title compound 24 (15.87 g, 58%) as a colourless liquid (b.p. 105-106° C./30 mbar). 13C-NMR (100 MHz, CDCl3): δ=145.2; 120.5; 69.7; 42.0; 24.0; 20.0; 14.2; 13.6

Workup

  1. temperatureThe mixture is refluxed for 3 h
  2. customquenched with ice
  3. filtrationThe precipitate is filtered off by suction
  4. washwashed several times with diethyl ether
  5. extractionThe aqueous solution is extracted with diethyl ether (3×100 ml)
  6. dry with materialThe combined etheral extracts are dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue
  9. distillationby vacuum distillation

Sources & evidence

ORD record
ord-a1ece089d4504bcb8854c24971ce5ec0
Source dataset
uspto-grants-2002_02
Patent number
US06350878B1

Reaction notes

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