HCID 20337447, compound → HCID 86737026, compound

HRID 1706252Notes

Reaction equation

HRID 1706252 reaction equation
[OH:1][C:2]1[C:17]([CH:18]([CH3:28])[CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][C:5]2[O:6][C:7]([CH3:15])([CH3:14])[C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:4]=2[CH:3]=1>[Pd].C(O)C>[OH:1][C:2]1[C:17]([CH:18]([CH3:28])[CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:16][C:5]2[O:6][C:7]([CH3:14])([CH3:15])[C@@H:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]3[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 20337447HCID 20337447, compound

Product 1

HCID 86737026HCID 86737026, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.0 g. of dl-7,8,9,10-tetrahydro-2-hydroxy-6,6-dimethyl-3-(1-methyl-4-phenylbutyl)-6H-dibenzo[b,d]pyran in 75 ml. of ethanol is added 200 mg. of 5% palladium-on-carbon catalyst and the resulting mixture is hydrogenated at room temperature and 60 psig. (4.3 kg./cm2) until the theoretical amount of hydrogen is consumed. After filtering to remove the catalyst, the solvent was evaporated to provide the desired 6a,10a-cis compound.

Workup

  1. customis hydrogenated at room temperature
  2. custom(4.3 kg./cm2) until the theoretical amount of hydrogen is consumed
  3. filtrationAfter filtering
  4. customto remove the catalyst
  5. customthe solvent was evaporated
  6. customto provide the desired 6a,10a-cis compound

Sources & evidence

ORD record
ord-55b937efd5da45eabaa73371b838d25f
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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