Sodium hydride → HCID 22858136, compound

HRID 374395Notes

Reaction equation

HRID 374395 reaction equation
[H-].[Na+].C(O[C:12]1[CH:13]=[C:14]([C:19]2[C:20](O)=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:15]([OH:18])=[CH:16][CH:17]=1)CCCCCCC.I[CH2:27][CH:28]1[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[O:31][C:29]1=[O:30]>CN(C)C=O>[CH2:15]([O:18][C:22]1[CH:23]=[CH:24][C:19]([C:14]2[C:15]([O:18][CH2:27][C@H:28]3[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[O:31][C:29]3=[O:30])=[CH:16][CH:17]=[CH:12][CH:13]=2)=[CH:20][CH:21]=1)[CH2:14][CH2:19][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20].[CH2:15]([O:18][C:22]1[CH:23]=[CH:24][C:19]([C:14]2[C:15]([O:18][CH2:27][C@@H:28]3[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[O:31][C:29]3=[O:30])=[CH:16][CH:17]=[CH:12][CH:13]=2)=[CH:20][CH:21]=1)[CH2:14][CH2:19][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 18996495HCID 18996495, compoundHCID 18996512HCID 18996512, compound

Product 2

HCID 22858136HCID 22858136, compoundHCID 22858138HCID 22858138, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Thereafter, 0.09 g of 60% sodium hydride was suspended in 5 ml of dimethylformamide, and a solution of 0.63 g of 4'-octyloxybiphenol in 5 ml of dimethylformamide was added to the suspension, and the mixture was stirred at room temperature for 1 hr to conduct a reaction. To the resultant solution was added 0.60 g of 2-iodomethyl-5,5-dimethyl-δ-valerolactone, and stirring was continued at room temperature for two days to conduct a reaction. The reaction mixture was poured into ice water, and the reaction product was extracted with diethyl ether. The extract was washed three times with water and dried over magnesium sulfate, the solvent was removed by distillation under a reduced pressure to obtain a crude product, and the crude product was purified by a silica gel column chromatography to 0.58 g of 2-(4'-octyloxybiphenyloxymethyl)-5,5-dimethyl-δ-valerolactone. The product was subjected to optical resolution by a liquid chromatography, and both components thus obtained were each recrystallized from ethanol to obtain 0.20 g of (2R)-2-(4 '-octyloxybiphenyloxymethyl)-5,5-dimethyl-δ-valerolactone and 0.11 g of (2S)-2-(4'-octyloxybiphenyloxymethyl)-5,5-dimethyl-δ-valerolactone, respectively.

Workup

  1. customa reaction
  2. stirringstirring
  3. waitwas continued at room temperature for two days
  4. customa reaction
  5. extractionthe reaction product was extracted with diethyl ether
  6. washThe extract was washed three times with water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was removed by distillation under a reduced pressure
  9. customto obtain a crude product
  10. customthe crude product was purified by a silica gel column chromatography to 0.58 g of 2-(4'-octyloxybiphenyloxymethyl)-5,5-dimethyl-δ-valerolactone
  11. customboth components thus obtained
  12. customeach recrystallized from ethanol

Sources & evidence

ORD record
ord-dfa46383ba6c4f3fa354116c115b841d
Source dataset
uspto-grants-1996_01
Patent number
US05480580

Reaction notes

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