Dimethyl Sulfoxide → HCID 54487108, compound

HRID 247245Notes

Reaction equation

HRID 247245 reaction equation
[H-].[Na+].[Br-].[F:4][C:5]([F:32])([F:31])[C:6]1[CH:11]=[CH:10][C:9]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1.[CH3:33][C:34]([CH3:53])([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:41]=1)[CH:35]=O.O.[CH3:55]S(C)=O>>[CH3:33][C:34]([CH3:53])([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:41]=1)[CH:35]=[CH:55][C:9]1[CH:8]=[CH:7][C:6]([C:5]([F:4])([F:31])[F:32])=[CH:11][CH:10]=1

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 24758Sodium hydrideHCID 138494092,2-Dimethyl-3-[(3-phenoxyphenyl)methoxy]propanalHCID 21284086HCID 21284086, compound

Product 1

HCID 54487108HCID 54487108, compound

Procedure

A suspension of sodium hydride (0.1 g) in dry dimethylsulphoxide (15 cm3) was heated to 65° C. for a period of 11/2 hours. After cooling to the ambient temperature (ca. 25° C.) 4-trifluoromethylphenyltriphenylphosphonium bromide (1.75 g) was added in portions, and the mixture was stirred for a further hour. A solution of 2,2-dimethyl-3-(3-phenoxybenzyloxy)propan-1-al in dimethylsulphoxide (15 cm3) was then added, and after stirring for 2 hours, the reaction mixture was poured into water and extracted into ethylacetate. The extracts were combined, washed with water and dried over anhydrous magnesium sulphate, and concentrated by evaporation of the solvent to yield an orange oil. This was flash chromatographed on a silica gel column with dichloromethane as eluent to yield 3,3-dimethyl-1-(4-trifluoromethylphenyl)-4-(3-phenoxybenzyloxy)but-1-ene (0.7 g) as a colourless oil, identified by nmr spectroscopy as an impure mixture of the Z and E isomers (ratio 3:1).

Workup

  1. additionwas added in portions
  2. stirringafter stirring for 2 hours
  3. extractionextracted into ethylacetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated by evaporation of the solvent
  7. customto yield an orange oil
  8. customThis was flash chromatographed on a silica gel column with dichloromethane as eluent

Sources & evidence

ORD record
ord-4950abf2c207482da618089bee82996d
Source dataset
uspto-grants-1987_11
Patent number
US04705900

Reaction notes

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