HCID 86593734, compound → HCID 86593738, compound

HRID 272103Notes

Reaction equation

HRID 272103 reaction equation
[CH2:1]([O:8][CH:9]1[CH:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:11]([OH:39])[C:10]1([OH:43])[CH2:40][CH2:41][CH3:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.CC(C)=O>[CH2:1]([O:8][CH:9]1[CH:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:12]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:11]([O:39][CH2:5][CH2:6][CH3:7])[C:10]1([O:43][C:1](=[O:8])[CH2:2][CH2:3][CH3:4])[CH2:40][CH2:41][CH3:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 86593734HCID 86593734, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86593738HCID 86593738, compoundYield 123.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

The allyl ether 21 (182 mg, 0.26 mmol) was dissolved in a mixture of 7 mL ethanol and 1 mL acetone and 18 mg Wilkinson catalyst (19 μmol) was added. The mixture was stirred in a hydrogen atmosphere for 3 days, before the solvents were removed under reduced pressure. The residue was chromatographed by preparative HPLC (95% MeOH, 40 mL/min, tRet=35.00 min) to give 26 as a colorless solid(108 mg, 0.16 mmol; 59.2% yield).

Workup

  1. additionwas added
  2. customwere removed under reduced pressure
  3. customThe residue was chromatographed by preparative HPLC (95% MeOH, 40 mL/min, tRet=35.00 min)

Sources & evidence

ORD record
ord-125dcb4eb9d34d73974a6846c0028878
Source dataset
uspto-grants-2008_11
Patent number
US07453006B2

Reaction notes

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