HCID 54358329, compound → HCID 54316182, compound

HRID 260303Notes

Reaction equation

HRID 260303 reaction equation
[CH2:1]([CH:4]1[CH2:28][C:27]2[C@:22]([CH3:30])([CH2:23][CH2:24][C:25](=[O:29])[CH:26]=2)[C@@H:21]2[C@@H:5]1[C@H:6]1[C@:18]([CH3:31])([CH2:19][CH2:20]2)[C@@H:9]([C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1)[CH:2]=[CH2:3]>[Rh](Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[CH2:1]([CH:4]1[CH2:28][C:27]2[C@:22]([CH3:30])([CH2:23][CH2:24][C:25](=[O:29])[CH:26]=2)[C@@H:21]2[C@@H:5]1[C@H:6]1[C@:18]([CH3:31])([CH2:19][CH2:20]2)[C@@H:9]([C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 54358329HCID 54358329, compound

Product 1

HCID 54316182HCID 54316182, compound

Reagents, catalysts & solvents 2

HCID 86736741HCID 86736741, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g. of the 7-allyl-enone 14, 5 ml. EtOAc and 50 mg. triphenylphosphine rhodium chloride (Wilkinson's catalyst) were allowed to stir two hours (under H2 atmosphere). The reaction products were filtered through 25 ml. silica gel, and evaporated to dryness to yield fairly pure title product, 18, as confirmed by proton NMR.

Workup

  1. filtrationThe reaction products were filtered through 25 ml
  2. customsilica gel, and evaporated to dryness

Sources & evidence

ORD record
ord-59fc9077066f424a834f6849e19e4205
Source dataset
uspto-grants-1996_06
Patent number
US05527807

Reaction notes

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