Hydrochloric Acid → HCID 19822214, compound

HRID 1030400Notes

Reaction equation

HRID 1030400 reaction equation
O1CCCC1.[CH3:6][O:7][CH2:8][O:9][C:10]1[C:11]([CH3:35])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([C:22](OCC)=[O:23])[CH2:14][CH2:13]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(OCC)(=O)C>[CH3:6][O:7][CH2:8][O:9][C:10]1[C:11]([CH3:35])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH2:22][OH:23])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:14][CH2:13]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 19822220HCID 19822220, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19822214HCID 19822214, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10 ml of tetrahydrofuran containing 3.3 g of ethyl 6-methoxymethoxy-5,7,8-trimethyl-2-octylchroman-2-carboxylate (prepared as described in Preparation 12) were added dropwise to a mixture of 0.45 g of lithium aluminum hydride and 30 ml of tetrahydrofuran under a nitrogen stream, and whilst ice-cooling. The resulting mixture was stirred for 3 hours at room temperature. Ethyl acetate and 5% w/v aqueous hydrochloric acid were then added to the reaction mixture, whilst ice-cooling, and the organic layer was separated. Then the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give the title compound.

Workup

  1. temperaturecooling
  2. additionwere then added to the reaction mixture, whilst ice-
  3. temperaturecooling
  4. customthe organic layer was separated
  5. extractionThen the aqueous layer was extracted with ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-396ef0e92c914439a09aeb17bb45fea6
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

Loading…