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

HRID 1589993Notes

Reaction equation

HRID 1589993 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Z-4-(5-acetoxy-3-methyl-pent-3-en-1-ynyl)-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: 136.36 (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).

Workup

  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

Sources & evidence

ORD record
ord-d883ae9bbcfb496ba62196e06edc3dbb
Source dataset
uspto-grants-1993_04
Patent number
US05201931

Reaction notes

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