Tetrahydrofuran → HCID 57226488, compound

HRID 47320Notes

Reaction equation

HRID 47320 reaction equation
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C:25](=[O:27])[CH2:24][CH2:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]([Mg]Br)=[CH2:29].[Cl-].[NH4+].[CH2:34]1COC[CH2:35]1>>[C:1]([O:20][CH2:21][C@@H:22]([OH:26])[CH2:23][CH2:24][C:25]([CH:28]=[CH2:29])([OH:27])[CH:34]=[CH2:35])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 2733809HCID 2733809, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 57226488HCID 57226488, compound

Procedure

26.9 g of (5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone was dissolved in 200 ml THF, 300 ml solution of 1 M vinylmagnesium bromide in THF was added thereto at room temperature, and it was stirred for 1.5 hr under heating and reflux. After the reaction was completed, saturated aqueous ammonium chloride was added thereto under ice-cooling, extracted with ethyl acetate, and then washed twice with brine. The solvent was removed and the resulting residue was purified by silica gel column chromatography to give 13.0 g of (2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. temperatureunder ice-cooling
  4. extractionextracted with ethyl acetate
  5. washwashed twice with brine
  6. customThe solvent was removed
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bf64994253ce43c098efe7553abe41c8
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

Loading…