HCID 178444495, compound → HCID 178444497, compound

HRID 1673167Notes

Reaction equation

HRID 1673167 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH:18]3[O:21][C:20](=[O:22])[CH2:19]3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:23]([C@H:28]1[CH2:33][CH2:32][C@H:31]([C@@H:34]2[CH2:39][CH2:38][C@H:37]([CH:40]3[O:43][C:42](=[O:44])[CH2:41]3)[CH2:36][CH2:35]2)[CH2:30][CH2:29]1)[CH2:24][CH2:25][CH2:26][CH3:27]>C(OCC)(=O)C>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH:18]3[O:21][C:20](=[O:22])[CH2:19]3)[CH2:14][CH2:13]2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:23]([C@H:28]1[CH2:29][CH2:30][C@H:31]([C@@H:34]2[CH2:39][CH2:38][C@H:37]([CH:40]3[O:43][C:42](=[O:44])[CH2:41]3)[CH2:36][CH2:35]2)[CH2:32][CH2:33]1)[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 178444495HCID 178444495, compoundHCID 178444496HCID 178444496, compound

Product 1

HCID 178444497HCID 178444497, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

Ethyl acetate (40 mL) was added to the mixture of 4-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-2-oxetanone and 4-(cis-4-(trans-4-pentylcyclohexyl)cyclohexyl)-2-oxetanone (mixing ratio: 98/2, 10.8 g, 28.1 mmol) synthesized in Example 4 and coarsely purified with silica gel chromatography, to dissolve the mixture at 30° C., followed by cooling to −20° C. Crystals deposited after lapsing 5 minutes were suction-filtered and dried under reduced pressure to provide 4-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-2-oxetanone/4-(cis-4-(trans-4-pentylcyclohexyl)cyclohexyl)-2-oxetanone=99.9/0.1 (8.3 g, 25.8 mmol, yield: 92%). Ethyl acetate (30 mL) was added to the resulting crystals, and the same operation was performed to provide 4-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-2-oxetanone (trans-isomer: 100%, 7.3 g, 24.2 mmol, yield: 94%).

Workup

  1. customsynthesized in Example 4
  2. customcoarsely purified with silica gel chromatography
  3. dissolutionto dissolve the mixture at 30° C.
  4. filtrationwere suction-filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1e3f3b0771df4f26a337b2dd7b574bb8
Source dataset
uspto-grants-2011_08
Patent number
US07999123B2

Reaction notes

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