Water → HCID 86748240, compound

HRID 2379575Notes

Reaction equation

HRID 2379575 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][CH2:18][CH:17](O)[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH3:23][O:24]S(OC)(=O)=O.O>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([O:24][CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 6497Dimethyl Sulfate2×HCID 14798Sodium Hydroxide2×HCID 18957485HCID 18957485, compound

Product 1

HCID 86748240HCID 86748240, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

3-(3-Cyclopentyloxy-4-methoxyphenyl)-cyclopentan-1-ol (predominantly cis, 130 mg, 0.47 mmol) (E9) in methylene chloride (5 ml) was stirred vigorously with aqueous sodium hydroxide (50%, 0.2 ml), tetrabutylammonium bromide (3 mg) and dimethylsulfate (0.1 ml, 1.05 mmol) under an argon atmosphere. The resulting mixture was stirred at room temperature for 24 hr, whereupon additional aqueous sodium hydroxide (0.2 ml) , tetrabutylammonium bromide (3 mg) and dimethylsulfate (0.1 ml) were added. After an additional 72 hr, the mixture was poured into water and extracted with methylene chloride. The extracts were dried (sodium sulfate) and concentrated under reduced pressure. Purification by flash chromatography, eluting with 1.5:1 ether/hexanes, provided the title compound as an oil.

Workup

  1. additionwere added
  2. extractionextracted with methylene chloride
  3. dry with materialThe extracts were dried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography
  6. washeluting with 1.5:1 ether/hexanes

Sources & evidence

ORD record
ord-a11e7a748bf64eac909e1a6ccb687f6d
Source dataset
uspto-grants-1994_11
Patent number
US05362915

Reaction notes

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