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

HRID 345891노트

반응식

HRID 345891 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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° 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.

후처리

  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

출처 및 근거

ORD 기록
ord-c70f000417f641b2925d2d3d94cd306b
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059611

반응 노트

불러오는 중…