Propyltriphenylphosphonium bromide → 4-(5-But-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690728Notes

Reaction equation

HRID 1690728 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].[CH3:24][C:25]1([CH3:43])[CH:34]([N:35]2[C:39]([CH:40]=O)=[CH:38][N:37]=[CH:36]2)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[O:42])[O:26]1>C1COCC1>[CH:40]([C:39]1[N:35]([CH:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](=[O:42])[O:26][C:25]2([CH3:43])[CH3:24])[CH:36]=[N:37][CH:38]=1)=[CH:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 80374Propyltriphenylphosphonium bromideHCID 248026903-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde

Product 1

HCID 669064414-(5-But-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of propyltriphenylphosphonium bromide (0.157 g, 0.41 mmol) in THF (1 mL) at −78° C. is added sodium hexamethyldisilylamide (1M in THF, 0.44 mL, 0.44 mmol) and the mixture is allowed to warm to ambient temperature over 10 min. This solution is cooled to −20° C. and 3-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde (0.10 g, 0.37 mmol) in THF (0.2 mL) is added. The cooling bath is removed and the mixture is stirred at ambient temperature overnight, then filtered. The filtrate is concentrated in vacuo to give the crude 4-(5-but-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one which is used in the next step without further purification; MS (ESI) m/z 297.1 (M+H).

Workup

  1. temperatureThis solution is cooled to −20° C.
  2. customThe cooling bath is removed
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-72087c82a35f4611ae672d52c11119f3
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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