Water → HCID 67102642, compound

HRID 901069Notes

Reaction equation

HRID 901069 reaction equation
[Br-].[PH4+].C1([C:9](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:10][O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])C=CC=CC=1.[H-].[Na+].[CH3:32][C:33]1[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[C:34]=1[CH2:35][O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH:40]=O.O>CS(C)=O>[CH2:10]([O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH:16]=[CH:40][C:39]1[CH:42]=[CH:43][CH:44]=[C:37]([O:36][CH2:35][C:34]2[C:33]([CH3:32])=[CH:48][CH:47]=[CH:46][C:45]=2[CH3:49])[CH:38]=1)[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 57892224HCID 57892224, compoundHCID 86608894HCID 86608894, compound2×

Product 1

HCID 67102642HCID 67102642, compoundYield 195.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
26.700000762939453 °C

Procedure

A mixture of triphenylethylvalerate phosphonium bromide (Step A, 13.29 g, 28.2 mmol) and sodium hydride (0.745 g, 31.0 mmol) in dimethyl sulfoxide (40 ml) was stirred for 30 minutes under nitrogen. The reaction mixture was heated to 26.7° C. and 3-(2,6-Dimethylbenzyloxy)benzaldehyde (5.00 g, 20.8 mmol) diluted in dimethyl sulfoxide (20 ml) was added dropwise over 4 minutes. The reaction mixture was stirred for 3 hours at 50° C. A mixture of triphenylethylvalerate phosphonium bromide (Step A, 5.56 g, 118 mmol) and sodium hydride (0.312 g) in dimethyl sulfoxide (15 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 6 hours at 50° C., cooled to room temperature and poured over ice (60 g) and water (60 ml) mixture. The aqueous mixture was extracted with ethyl acetate (3×150 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated to afford the 14.3 g of brown oil. The oil was dissolved in 30 ml of hexane:ethyl acetate (95:5) and chromatographed on a Biotage 75S silica gel column to give 5.8 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 3.74 g (51%) of a dark yellow oil.

Workup

  1. additionwas added dropwise over 4 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 6 hours at 50° C.
  6. temperaturecooled to room temperature
  7. extractionThe aqueous mixture was extracted with ethyl acetate (3×150 ml)
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4b39ea199acd475186485ac0f5540624
Source dataset
uspto-grants-2008_04
Patent number
US07361686B2

Reaction notes

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