HCID 13364568, compound → HCID 19848840, compound

HRID 1905117Notes

Reaction equation

HRID 1905117 reaction equation
C([O:8][C:9]1[C:14]2[C:15]([CH2:22][C:23]([O:25][CH2:26]C)=[O:24])([OH:21])[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[CH:12]=[C:11]([C:28]([CH3:36])([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:10]=1)C1C=CC=CC=1.[H][H]>CO>[OH:21][C:15]1([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:14]2[C:9]([OH:8])=[CH:10][C:11]([C:28]([CH3:35])([CH3:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:12][C:13]=2[O:18][C:17]([CH3:19])([CH3:20])[CH2:16]1

Participants

4

Reactant 2

HCID 13364568HCID 13364568, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19848840HCID 19848840, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 655 mg (1.37 mmole) 5-benzyloxy-4-ethoxycarbonylmethyl-4-hydroxy-2,2-dimethyl-7(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran, 133 mg 5% palladium-on-calcium carbonate and 50 ml methanol was hydrogenated at 38 psi (2.7 kg/cm2) until hydrogen uptake ceased. The mixture was filtered, the filtrate evaporated in vacuo and the residual oil taken up in hexane. Upon cooling, crystals formed which were collected by filtration, 66 mg. The mother liquor was evaporated in vacuo to an oil, pentane added and the mixture refrigerated overnight. Filtration gave an additional 179 mg of product. 1H-NMR(CDCl3)ppm(delta): 3.00 (dd, 2H), 3.20 (s, 2H), 3.70 (s, 3H), 4.90 (s, 1H), 6.35 (m, 2H), 7.65 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. temperatureUpon cooling
  4. customcrystals formed which
  5. filtrationwere collected by filtration, 66 mg
  6. customThe mother liquor was evaporated in vacuo to an oil, pentane
  7. additionadded
  8. customthe mixture refrigerated overnight
  9. filtrationFiltration

Sources & evidence

ORD record
ord-2f963dc42f7f40a193064970cc6f9375
Source dataset
uspto-grants-1989_06
Patent number
US04841078

Reaction notes

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