Water → HCID 89483989, compound

HRID 589242Notes

Reaction equation

HRID 589242 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CC([O-])(C)C.[K+].[Br:36][C:37]1[CH:38]=[C:39]([C:50]2[CH:57]=[CH:56][C:53]([CH:54]=O)=[CH:52][CH:51]=2)[S:40][C:41]=1[C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1.O>C1COCC1>[Br:36][C:37]1[CH:38]=[C:39]([C:50]2[CH:51]=[CH:52][C:53](/[CH:54]=[CH:2]/[CH:3]=[CH:4]/[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:56][CH:57]=2)[S:40][C:41]=1[C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2724860HCID 2724860, compoundHCID 23665647Potassium tert-butoxideHCID 89479720HCID 89479720, compound

Product 1

HCID 89483989HCID 89483989, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.83 g (23.6 mmol) of Cinnamyltriphenylphosphonium bromide was added to 2.70 g (24.10 mmol) of t-BuOK in 100 mL THF and the resulting solution was stirred at RT for 30 min. The reaction mixture was cooled to 0° C. and 8 g (21.4 mmol) of the aldehyde (62) was added in 35 mL THF. The solution was warmed to RT and stirred for 5 hrs. The solution was poured into 200 mL water. The precipitated product was separated by filtration to give 7.5 g (74% yield) of pure target molecule.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureThe solution was warmed to RT
  3. stirringstirred for 5 hrs
  4. customThe precipitated product was separated by filtration
  5. customto give 7.5 g (74% yield) of pure target molecule

Sources & evidence

ORD record
ord-d44f683b5853434f97be1746f8b83125
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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