Acetic Acid → HCID 67826073, compound

HRID 2379574Notes

Reaction equation

HRID 2379574 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C.[OH-].[K+]>CO.O.O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 5462977Diethyl azodicarboxylateHCID 18957485HCID 18957485, compound

Product 1

HCID 67826073HCID 67826073, compoundYield 55.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Cyclopentyloxy-4-methoxyphenyl) -cyclopentan-1-ol, (predominantly cis, 160 mg, 0.58mmol) (E9) in freshly distilled tetrahydrofuran (5 ml) was stirred vigorously with diethylazodicarboxylate (96μl 0.58 mmol), triphenylphosphine (152 mg, 0.58mmol) and glacial acetic acid (35μl, 0.61 mmol) under an argon atmosphere at room temperature for 24 hr. The liquids were removed under reduced pressure, with purification by flash chromatography, eluting with 2:1 hexanes/ether, providing and trans acetate as an oil (133 mg, 72%). This oil (133 mg, 0.42 mmol) in methanol (2 ml) was treated with potassium hydroxide (89%, 52 mg 0.82 mmol) in water (0.3 ml) for 1 hr. The mixture was partitioned between ether and water, the ether was dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 1:1 hexanes/ether, provided the title compound as an oil (89 mg, 55.6%).

Workup

  1. customThe liquids were removed under reduced pressure, with purification by flash chromatography
  2. washeluting with 2:1 hexanes/ether
  3. customproviding
  4. customThe mixture was partitioned between ether and water
  5. dry with materialthe ether was dried (potassium carbonate)
  6. customthe solvent was removed in vacuo
  7. customPurification by flash chromatography
  8. washeluting with 1:1 hexanes/ether

Sources & evidence

ORD record
ord-3fb1e0795730476d8cc6861bdd16e3bb
Source dataset
uspto-grants-1994_11
Patent number
US05362915

Reaction notes

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