Diethyl Ether → HCID 22857729, compound

HRID 2259511Notes

Reaction equation

HRID 2259511 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH:18]=1)[O:11][CH2:12][C:13](=[CH2:16])[CH2:14][OH:15].[CH3:31]COCC>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH:18]=1)[O:11][CH2:12][C:13]1([CH2:14][OH:15])[CH2:31][CH2:16]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 22857730HCID 22857730, compound

Product 1

HCID 22857729HCID 22857729, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., Pd(OAc)2 (500 mg) and ~0.4M CH2N2 in ether (1.84) were added portionwise and simultaneously to a solution of the allylic alcohol of Step 4 (20.45 g, 43.0 mmol) in 80 mL of THF. When the reaction was complete, the mixture was filtered through a small pad of silica and concentrated. The residue was purified by flash chromatography on silica with EtOAc:toluene 15:85 to give 12.40 g (59%) of the title product.

Workup

  1. filtrationthe mixture was filtered through a small pad of silica
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica with EtOAc:toluene 15:85

Sources & evidence

ORD record
ord-ad11f232486646b5a0fac81b1bc8b84a
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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