Methanol → Z-4-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-3,4-epoxy-3,5,5-trimethylcyclohexan-1-ol

HRID 440223노트

반응식

HRID 440223 반응식
C([O:4][CH2:5]/[CH:6]=[C:7](/[CH3:21])\[C:8]#[C:9][C:10]12[O:20][C:11]1([CH3:19])[CH2:12][CH:13]([OH:18])[CH2:14][C:15]2([CH3:17])[CH3:16])(=O)C.C([O-])([O-])=O.[K+].[K+].CO>O>[OH:4][CH2:5]/[CH:6]=[C:7](/[CH3:21])\[C:8]#[C:9][C:10]12[O:20][C:11]1([CH3:19])[CH2:12][CH:13]([OH:18])[CH2:14][C:15]2([CH3:17])[CH3:16]

참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 22406461Z-4-(5-acetoxy-3-methyl-pent-3-en-1-ynyl)-3,4-epoxy-3,5,5-trimethylcyclohexan-1-ol

생성물 1

HCID 19768854Z-4-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-3,4-epoxy-3,5,5-trimethylcyclohexan-1-ol수율 69.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of Z-4-(5-acetoxy-3-methyl-pent-3-en-1ynyl)-3,4-epoxy-3,5,5-trimethylcyclohexan-1-ol (36 mg, 0.12 mmol), K2CO3 (26 mg, 0.18 mmol), methanol (1 mL) and H2O (1 mL) was stirred at room temperature for 1 h. It was then concentrated by evaporation and the residue was diluted with H2O and extracted with CHCl3. The organic extract was dried over anhydrous Na2SO4. Evaporation of solvent gave compound (5) as a colorless oil (21 mg, 69%), ir: 3620 (sharp, medium, OH) and 3450 (broad, weak, OH) cm-1; 1H nmr d: 5.87 (ddq, J=6.7, 6.7, 1.4 Hz, 1H, =CH), 4.27 (dd, J=6.7, 1.0 Hz, 2H, CH2O), 3.82 (m, 1H, CHOH), 2.18 (ddd, J=14.8, 6.8, 1.4 Hz, 1H, CH2), 1.86 (m, 3 H, vinyl CH3), 1.79 (dd, J=14.8, 9.0 Hz, 1H, CH2), 1.46 (s, CH3), 1.36 (ddd, J=12.7, 4.1, 1.5 Hz, 1H, CH2), 1.16 and 1.17 (2s, 6H, 2CH3); 13C nmr d: 136.63 (d, =CH), 119.95 (s, =C), 90.95 and 83.99 (2s, 2 acetylenic C), 65.08 and 64.52 (2s, C--O--C), 63.29 (d, CHOH), 61.15, 41.84 and 38.16 (3t, 3 CH2), 34.83 (s, C), 27.03, 25.60, 22.98 and 22.92 (4q, 4CH3); ms (NH4Cl CI) m/z: 268 (M+18), 251 (M+1), 233 (M-17).

후처리

  1. concentrationIt was then concentrated by evaporation
  2. additionthe residue was diluted with H2O
  3. extractionextracted with CHCl3
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous Na2SO4
  6. customEvaporation of solvent

출처 및 근거

ORD 기록
ord-083e43ce1ea9445fab422f9cc74aa46a
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05518995

반응 노트

불러오는 중…