Pyridine → HCID 86752788, compound

HRID 481333Notes

Reaction equation

HRID 481333 reaction equation
[OH:1][CH:2]([CH:27]([OH:29])[CH3:28])[CH:3]=[CH:4][C:5]([O:7][CH:8]1[CH2:15][CH2:14][C:11]2([O:13][CH2:12]2)[CH:10]([C:16]2([CH3:24])[CH:18]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[O:17]2)[CH:9]1[O:25][CH3:26])=[O:6].[C:30](OC(=O)C)(=[O:32])[CH3:31].N1C=CC=CC=1.[CH2:43]([O:45]CC)[CH3:44]>CN(C)C1C=CN=CC=1.ClCCl>[C:30]([O:1][CH:2]([CH:27]([O:29][C:43](=[O:45])[CH3:44])[CH3:28])[CH:3]=[CH:4][C:5]([O:7][CH:8]1[CH2:15][CH2:14][C:11]2([O:13][CH2:12]2)[CH:10]([C:16]2([CH3:24])[CH:18]([CH2:19][CH:20]=[C:21]([CH3:22])[CH3:23])[O:17]2)[CH:9]1[O:25][CH3:26])=[O:6])(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 3035611HCID 3035611, compound

Product 1

HCID 86752788HCID 86752788, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(4,5-dihydroxy-2-hexenoyloxy)-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (which is the same compound as "WF 2015A" and was prepared in the same manner as that described in European Patent Application Publication No. 0314401) (34 mg), acetic anhydride (34 μl), pyridine (30 μl), and 4-dimethylaminopyridine (1 mg) in dichloromethane (0.7 ml) was stirred overnight at ambient temperature. The mixture was diluted with diethyl ether and washed with brine (X3). The organic layer was dried and concentrated in vacuo to yield 6-(4,5-diacetoxy-2-hexenoyloxy)-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (41.7 mg) as a colorless oil.

Workup

  1. customwas prepared in the same manner as
  2. washwashed with brine (X3)
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59071a890bb942838dae68127d4f5c27
Source dataset
uspto-grants-1998_08
Patent number
US05789405

Reaction notes

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