Water → HCID 67102949, compound

HRID 901067Notes

Reaction equation

HRID 901067 reaction equation
[Br-].[PH4+].C1([C:9](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:10][O:11][C:12](=[O:16])[CH2:13][CH2:14][CH3:15])C=CC=CC=1.[H-].[Na+].[CH3:31][C:32]1[CH:47]=[CH:46][CH:45]=[C:44]([CH3:48])[C:33]=1[CH2:34][O:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=O.O>CS(C)=O>[CH2:10]([O:11][C:12](=[O:16])[CH2:13][CH2:14][CH:15]=[CH:39][C:38]1[CH:41]=[CH:42][CH:43]=[C:36]([O:35][CH2:34][C:33]2[C:32]([CH3:31])=[CH:47][CH:46]=[CH:45][C:44]=2[CH3:48])[CH:37]=1)[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 57892224HCID 57892224, compoundHCID 86612455HCID 86612455, compound2×

Product 1

HCID 67102949HCID 67102949, compoundYield 228%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
26.700000762939453 °C

Procedure

A mixture of triphenylethylbutyrate phosphonium bromide (10.06 g, 22 mmol) and sodium hydride (0.581 g, 24.2 mmol) in dimethyl sulfoxide (45 ml) was stirred for 30 minutes under nitrogen. The reaction mixture was heated to 26.7° C. and 3-(2,6-Dimethylbenzyloxy)benzaldehyde (3.89 g, 16.2 mmol) diluted in dimethyl sulfoxide (15 ml) was added dropwise over 3 minutes. The reaction mixture was stirred for 3 hours at 50° C. A mixture of triphenylethylbutyrate phosphonium bromide (3.20 g, 70 mmol) and sodium hydride (0.185 g) in dimethyl sulfoxide (10 ml) was stirred under nitrogen for 30 minutes. This mixture was added, in bolus to the above reaction mixture at room temperature. The reaction mixture was stirred for Z hours at 50° C., cooled to room temperature and poured over ice (50 g) and water (50 ml) mixture. The aqueous mixture was extracted with ethyl acetate (3×125 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated to afford the 12.5 g of brown oil. The oil was dissolved in 30 ml of hexanes:ethyl acetate (95:5) and chromatographed on a Biotage 75S silica gel column to give 4.9 g of a yellow oil. The yellow oil was subjected to another silica gel column chromatography eluting with hexane:chloroform (1:1) to hexane:ethyl acetate (9:1) to afford 3.40 g (62%) of a faint yellow oil product which solidified upon standing.

Workup

  1. additionwas added dropwise over 3 minutes
  2. stirringThe reaction mixture was stirred for 3 hours at 50° C
  3. stirringwas stirred under nitrogen for 30 minutes
  4. additionThis mixture was added, in bolus to the above reaction mixture at room temperature
  5. stirringThe reaction mixture was stirred for Z hours at 50° C.
  6. temperaturecooled to room temperature
  7. extractionThe aqueous mixture was extracted with ethyl acetate (3×125 ml)
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4423a48fa6e34313a731ad6112c3a500
Source dataset
uspto-grants-2008_04
Patent number
US07361686B2

Reaction notes

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