1,2-Diethenylbenzene → (3S,4S)-3-Hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

HRID 703689Notes

Reaction equation

HRID 703689 reaction equation
[O:1]([C@@H:9]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:10][C@@H:11]1[O:14][C:13](=[O:15])[C@H:12]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[Si](C(C)(C)C)(C)C.C(C1C=CC=CC=1C=C)=C>CO>[CH2:16]([C@H:12]1[C@H:11]([CH2:10][C@@H:9]([OH:1])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[O:14][C:13]1=[O:15])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 666661,2-DiethenylbenzeneHCID 11583592HCID 11583592, compound

Product 1

HCID 9968521(3S,4S)-3-Hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.23 g of (3S,4S)-4-[(S)-2-(tert-butyldimethylsiloxy)tridecyl]-3-hexyl-2-oxetanone are dissolved in 6 ml of methanol and heated to reflux with the addition of 1.05 g of DOWEX 50W-X8 (acidic cation exchanger based on polymeric divinylbenzene containing sulphonic acid residues). The ion exchanger is filtered off and the filtrate is evaporated. The residue is chromatographed on silica gel. After recrystallization from hexane there is obtained (3S,4S)-3-hexyl-4-[(S)-2-hydroxytridecyl]-2-oxetanone of melting point 63°-64° C.

Workup

  1. temperatureheated
  2. filtrationThe ion exchanger is filtered off
  3. customthe filtrate is evaporated
  4. customThe residue is chromatographed on silica gel
  5. customAfter recrystallization from hexane

Sources & evidence

ORD record
ord-1178495d362e4b408dbf1d997d286271
Source dataset
uspto-grants-1991_01
Patent number
US04983746

Reaction notes

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