Diethyl Ether → HCID 131717628, compound

HRID 373248Notes

Reaction equation

HRID 373248 reaction equation
[O:1]([CH2:9][C@H:10]1[C@H:17]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:16][C@H:15]2[C@@H:11]1[CH2:12][C:13](C=O)=[CH:14]2)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Br-].C([CH2:31][CH2:32][CH2:33]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.C[C:54]([CH3:57])([O-:56])C.[K+].[N+](=C)=[N-].C[CH2:63][O:64]CC>>[O:1]([CH2:9][C@H:10]1[C@H:17]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:16][C@H:15]2[C@@H:11]1[CH2:12][C:13]([CH:31]=[CH:32][CH2:33][CH2:57][C:54]([O:64][CH3:63])=[O:56])=[CH:14]2)[Si:2]([C:5]([CH3:7])([CH3:6])[CH3:8])([CH3:4])[CH3:3]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 13565984HCID 13565984, compoundHCID 23665647Potassium tert-butoxideHCID 178525533HCID 178525533, compound

Product 1

HCID 131717628HCID 131717628, compound

Procedure

Commercially available (1S,5S,6S,7R)-6-(t-butyldimethylsiloxymethyl)-3-formyl -7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (1.00 g) (1) was reacted with an ylide which was prepared from (3-carboxypropyl)triphenylphosphine bromide and potassium t-butoxide. A crude carboxylic acid was obtained according to a usual work-up. The product was reacted with diazomethane in ether. A crude product obtained after a usual work-up was purified on a column chromatography (hexane/ethyl acetate=10/1) to give (1S,5S,6S,7R)-6-(t-butyldimethylsiloxymethyl)-3-[4-methoxycarbonyl-1(EZ)-butenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (2) as a colorless oily product. Yield: 0.85 g (67%)

Workup

  1. customA crude carboxylic acid was obtained
  2. customA crude product obtained after a usual work-up
  3. customwas purified on a column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-1cd2ec5604b84d19b166ad4b7c069b60
Source dataset
uspto-grants-1992_11
Patent number
US05162370

Reaction notes

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