Diethyl Ether → HCID 23182903, compound

HRID 986332Notes

Reaction equation

HRID 986332 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][Mg]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[Si:15]([O:22][CH:23]1[CH2:27][C:26](=[O:28])[CH:25]=[CH:24]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[Cl-].[Na+].CC[O:33]CC>>[Si:15]([O:22][C:23]1[C:24](=[O:33])[CH2:25][C:26]([OH:28])([CH2:11][CH2:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:27]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 5234Sodium ChlorideHCID 41316994-((tert-Butyl(dimethyl)silyl)oxy)cyclopent-2-en-1-oneHCID 5462224MagnesiumHCID 178419682HCID 178419682, compound

Product 1

HCID 23182903HCID 23182903, compound

Procedure

55 ml (39 mmoles) of a 0.71 M solution of 4-phenoxybutyl magnesium bromide prepared from 10.1 g (44 mmoles) of 4-phenoxy bromide and 1.07 g (44 mmoles) of magnesium in 60 ml of ether was taken, and in an atmosphere of nitrogen, a solution of 7.63 g (36 mmoles) of 4-t-butyldimethylsilyloxy-2-cyclopentenone in 20 ml of ether was added dropwise at -78° C., and the mixture was stirred for 4 hours. A saturated aqueous solution of sodium chloride was added to terminate the reaction. The reaction mixture was extracted with ether, washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was chromatographed on a silica gel column (hexane:AcOEt=12:1) to give 5.2 g (40%) of a low polarity, 1,2-adduct and 2.9 g (22%) of a high polarity 1,2-adduct. ##STR30##

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ether
  4. washwashed with an aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on a silica gel column (hexane:AcOEt=12:1)
  9. customto give 5.2 g (40%) of a low polarity, 1,2-adduct and 2.9 g (22%) of a high polarity 1,2-adduct

Sources & evidence

ORD record
ord-4bf158246f4847d49a979147cd1084f6
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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