4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)cyclohexane → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-formylcyclohexane

HRID 343543Notes

Reaction equation

HRID 343543 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:13]1([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:24]=2)[CH2:18][CH2:17][C:16]2([O:22][CH2:21][CH2:20][O:19]2)[CH2:15][CH2:14]1)#N.S(=O)(O)[O-:38].[Na+]>C1(C)C=CC=CC=1>[CH:32]1([O:31][C:25]2[CH:24]=[C:23]([C:13]3([CH:11]=[O:38])[CH2:18][CH2:17][C:16]4([O:19][CH2:20][CH2:21][O:22]4)[CH2:15][CH2:14]3)[CH:28]=[CH:27][C:26]=2[O:29][CH3:30])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 153920364-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)cyclohexaneHCID 21225700DiisobutylaluminumhydrideHCID 23665763Sodium Bisulfite

Product 1

HCID 153920374-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-formylcyclohexane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diisobutylaluminum hydride (1.0M in toluene, 8.13 mL, 8.13 mmol) was added dropwise to a solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)cyclohexane (1.16 g, 3.19 mmol) dissolved in toluene (20 mL) under an argon atmosphere. After 18 h at room temperature, saturated aqueous sodium bisulfite (100 mL) was added and the mixture was extracted three times with dichloromethane. The combined organic extract was washed with brine, was dried (potassium carbonate) and was evaporated. Purification by flash chromatography, eluting with 4:1 hexanes/ethyl acetate, provided a clear colorless oil. 1H NMR(400 MHz, CDCl3) δ 9.35 (s, 1H), 6.88 (br s, 2H), 6.80 (s, 1H), 4.73 (m, 1H), 3.95 (m, 4H), 3.85 (s, 3H), 2.33 (m, 2H), 2.10 (m, 2H), 1.57-1.99 (m, 12H).

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialwas dried (potassium carbonate)
  5. customwas evaporated
  6. customPurification by flash chromatography
  7. washeluting with 4:1 hexanes/ethyl acetate
  8. customprovided a clear colorless oil

Sources & evidence

ORD record
ord-a291c1a631004d9ea050ab67285a11d9
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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