Ethyl Acetate → HCID 59981114, compound

HRID 586680Notes

Reaction equation

HRID 586680 reaction equation
[CH3:1][C:2]12[C:8]([CH3:10])([CH3:9])[C:5]([C:11]([O:13][CH2:14][C@H:15]3[C@@H:17]([CH2:18][O:19][CH3:20])[C@@:16]3([CH3:33])[C:21]3[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[C:23]([CH:30]([CH3:32])[CH3:31])[CH:22]=3)=[O:12])([CH2:6][CH2:7]1)[O:4][C:3]2=[O:34].COCC1[C@H](CO)C1(C)C1C=C(C(C)C)C=C(C(C)C)C=1.CCOC(C)=O>CCCCCC>[CH3:1][C:2]12[C:8]([CH3:9])([CH3:10])[C:5]([C:11]([O:13][CH2:14][C@H:15]3[C@H:17]([CH2:18][O:19][CH3:20])[C@@:16]3([CH3:33])[C:21]3[CH:26]=[C:25]([CH:27]([CH3:28])[CH3:29])[CH:24]=[C:23]([CH:30]([CH3:32])[CH3:31])[CH:22]=3)=[O:12])([CH2:6][CH2:7]1)[O:4][C:3]2=[O:34].[CH3:1][C:2]12[C:8]([CH3:9])([CH3:10])[C:5]([C:11]([O:13][CH2:14][C@@H:15]3[C@@H:17]([CH2:18][O:19][CH3:20])[C@:16]3([CH3:33])[C:21]3[CH:26]=[C:25]([CH:27]([CH3:28])[CH3:29])[CH:24]=[C:23]([CH:30]([CH3:32])[CH3:31])[CH:22]=3)=[O:12])([CH2:6][CH2:7]1)[O:4][C:3]2=[O:34]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 69737302HCID 69737302, compoundHCID 86759826HCID 86759826, compound

Product 2

HCID 59981098HCID 59981098, compoundYield 41%HCID 59981114HCID 59981114, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following a procedure similar to that for the preparation of Intermediates 41 and 42 but using Intermediate 40a as the starting material and using 10% EtOAc in hexane as normal phase HPLC eluent afforded Intermediate 43a (25 mg, 45% yield) and Intermediate 44a (23 mg, 41% yield) as colorless oils:

Sources & evidence

ORD record
ord-361bca9f39114c01b5dbda2985dca5ad
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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