Dodecyl acetate → HCID 22165559, compound

HRID 1032283Notes

Reaction equation

HRID 1032283 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH2:25]([Si:27]([CH2:37][CH3:38])([CH2:35][CH3:36])[C:28]1[O:32][CH:31]=[C:30]([CH:33]=[O:34])[CH:29]=1)[CH3:26]>O1CCCC1>[OH:34][CH:33]([C:30]1[CH:29]=[C:28]([Si:27]([CH2:35][CH3:36])([CH2:37][CH3:38])[CH2:25][CH3:26])[O:32][CH:31]=1)[CH2:2][C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:3]

Participants

5

Reactant 3

HCID 8205Dodecyl acetateHCID 2724682Lithium diisopropylamideHCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

Product 1

HCID 22165559HCID 22165559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dodecyl acetate (240 mg, 1.04 mmol) in tetrahydrofuran (2 ml) was added to a solution of lithium diisopropylamide (1.04 mmol; =generated from 0.15 ml of diisopropylamine and 0.42 ml n-butyl lithium at -78°) in tetrahydrofuran (10 ml) at -78° under argon. After 1h, a solution of 5-triethylsilyl-3-furaldehyde (200 mg, 0.95 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 15h while the cooling bath attained room temperature. The mixture was quenched with water and was extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by a silica column using 20% ethyl ether/hexane to give the titled ester.

Workup

  1. customThe mixture was quenched with water
  2. extractionwas extracted thoroughly with ethyl acetate
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil which
  6. customwas purified by a silica column

Sources & evidence

ORD record
ord-1cd88f9ef7f94b2891d8a3102fcdad52
Source dataset
uspto-grants-1990_09
Patent number
US04957917

Reaction notes

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