Water → HCID 89483892, compound

HRID 589241Notes

Reaction equation

HRID 589241 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:28][C:29]1[CH:30]=[C:31]([C:42]2[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=2)[S:32][C:33]=1[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1.CC([O-])(C)C.[K+].O>C(Cl)(Cl)Cl.C1COCC1>[Br:28][C:29]1[CH:30]=[C:31]([C:42]2[CH:49]=[CH:48][C:45](/[CH:46]=[CH:2]/[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:44][CH:43]=2)[S:32][C:33]=1[C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2734970Benzyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 89479720HCID 89479720, compound

Product 1

HCID 89483892HCID 89483892, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyltriphenylphosphonium bromide (23.7 g, 54.7 mmol) and (62) (17 g, 45.5 mmol) was dispersed in chloroform (300 mL) and stirred at RT under argon atmosphere for 15 min. A solution of t-BuOK (10.3 g, 91 mmol) in anhydrous THF (80 mL) was added dropwise. The reaction mixture was stirred at RT for 3 h. Then water was added, followed by extraction with chloroform. The combined extracts were dried over anhydrous MgSO4 and solvent evaporated to half of its initial volume by rotary evaporation; the resulting light yellow precipitation was filtered and dried (9.63 g; 47% yield).

Workup

  1. stirringThe reaction mixture was stirred at RT for 3 h
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4 and solvent
  4. customevaporated to half of its initial volume
  5. customby rotary evaporation
  6. customthe resulting light yellow precipitation
  7. filtrationwas filtered
  8. customdried (9.63 g; 47% yield)

Sources & evidence

ORD record
ord-f283da58b73a4cf4b714d92e459ffb37
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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