Furan → (1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one

HRID 407837Notes

Reaction equation

HRID 407837 reaction equation
Cl[CH:2]1[C:6](=[O:7])[C:5]([C:8]2[C:13]([CH2:14][CH3:15])=[CH:12][C:11]([CH3:16])=[CH:10][C:9]=2[CH2:17][CH3:18])=[C:4]([O:19][CH3:20])[CH2:3]1.N12CCCN=C1CCCCC2.[O:32]1[CH:36]=[CH:35][CH:34]=[CH:33]1>>[CH2:14]([C:13]1[CH:12]=[C:11]([CH3:16])[CH:10]=[C:9]([CH2:17][CH3:18])[C:8]=1[C:5]1[C:6](=[O:7])[CH:2]2[CH:3]([C:4]=1[O:19][CH3:20])[CH:36]1[O:32][CH:33]2[CH:34]=[CH:35]1)[CH3:15]

Participants

4

Reactant 3

HCID 8029Furan2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 672841155-Chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone

Product 1

HCID 67283452(1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one

Procedure

To a stirred solution of 5-chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone (0.530 g, 1.81 mmol) in furan (40 ml) at room temperature is added by syringe pump over two hours a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.540 ml, 3.62 mmol) in furan (10 ml). The reaction is stirred at room temperature for a further 30 minutes and then evaporated to dryness under reduced pressure. The residue is diluted with water (50 ml), 2 M aqueous hydrochloric acid (25 ml) is added and the mixture is extracted with ethyl acetate (3×50 ml). The combined organic extracts are washed with brine (20 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one.

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue is diluted with water (50 ml), 2 M aqueous hydrochloric acid (25 ml)
  3. additionis added
  4. extractionthe mixture is extracted with ethyl acetate (3×50 ml)
  5. washThe combined organic extracts are washed with brine (20 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated to dryness under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2c984bbbc1ab48eb8fd751e8b3ea9827
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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