HCID 54358329, compound → HCID 54316182, compound

HRID 1077445Notes

Reaction equation

HRID 1077445 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 silica gel
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-be23218c92bb4e6a8af5c7f3cc2c9518
Source dataset
uspto-grants-1996_08
Patent number
US05543417

Reaction notes

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