Tetrahydrofuran → Benzenamine, 4-ethenyl-N,N-diphenyl-

HRID 1374479Notes

Reaction equation

HRID 1374479 reaction equation
[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCC[CH2:23]1.CC(C)([O-])C.[K+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[CH2:23])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 10869403Benzenamine, 4-ethenyl-N,N-diphenyl-

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 4-(diphenylamino)benzaldehyde (20.06 g, 73 mmol, Fluka Chemical Co., Milwaukee, Wis.), methyltriphenyl phosphonium bromide (26.22 g, 73 mmol) and dry tetrahydrofuran (450 mL) under nitrogen was added a 1M solution of potassium t-butoxide in tetrahydrofuran (80 mL, 80 mmol) over 5 minutes. The mixture was stirred for 17 hours at room temperature. Water (400 mL) was added and the tetrahydrofuran was removed under reduced pressure. The mixture was extracted with ether, and the combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude solid was purified by column chromatography on silica gel using a 50/50 mixture of methylene chloride and hexane to give a yellow solid that was further recrystallized once from hexane (15.37 g, 78%).

Workup

  1. customthe tetrahydrofuran was removed under reduced pressure
  2. extractionThe mixture was extracted with ether
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe crude solid was purified by column chromatography on silica gel using
  6. additiona 50/50 mixture of methylene chloride and hexane
  7. customto give a yellow solid
  8. customthat was further recrystallized once from hexane (15.37 g, 78%)

Sources & evidence

ORD record
ord-1bd48905ce6a4a6b94b191cdfcfa5114
Source dataset
uspto-grants-2007_01
Patent number
US07166010B2

Reaction notes

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