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

HRID 1681515ノート

反応式

HRID 1681515 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1311c4d139614cfc93e278371cd7def5
出典データセット
uspto-grants-1992_12
特許番号
US05171863

反応ノート

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