Dodecanal → 4-(5-Hydroxy-3-hexadecynyl)-2-triethylsilylfuran

HRID 1109884Notes

Reaction equation

HRID 1109884 reaction equation
C([Li])CCC.Br[C:7](Br)=[CH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])[O:14][CH:15]=1.[CH:24](=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O1CCCC1>[OH:36][CH:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:7]#[C:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])[O:14][CH:15]=1

Participants

5

Reactant 3

HCID 8194DodecanalHCID 150371054-(4,4-Dibromo-3-butenyl)-2-triethylsilylfuranHCID 178418339Butyllithium

Product 1

HCID 150371064-(5-Hydroxy-3-hexadecynyl)-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.42 ml, 1.04 mmol) was added dropwise to a solution of 4-(4,4-dibromo-3-butenyl)-2-triethylsilylfuran (200 mg, 0.51 mmol) in tetrahydrofuran (8 ml) at -78 degrees under argon. After 2 hours, a solution of 1-dodecanal (102 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane to give the titled alcohol.

Workup

  1. waitwas continued for 14 hours, while the cooling bath attained room temperature
  2. customThe mixture was quenched with water
  3. extractionwas extracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave a residue, which
  7. customwas purified by a silica column with 15% ethyl ether/hexane

Sources & evidence

ORD record
ord-142a973d50894237839980ccf72f19b7
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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