3-Dipropylamino-5-acetylchroman → 3-Dipropylamino-5-isopropenylchroman

HRID 264989Notes

Reaction equation

HRID 264989 reaction equation
[Li][CH2:2]CCC.[CH2:6]([N:9]([CH2:23][CH2:24][CH3:25])[CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:20](=O)[CH3:21])[O:12][CH2:11]1)[CH2:7][CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH2:6]([N:9]([CH2:23][CH2:24][CH3:25])[CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:20]([CH3:2])=[CH2:21])[O:12][CH2:11]1)[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 102212133-Dipropylamino-5-acetylchromanHCID 178418339Butyllithium

Product 1

HCID 190282133-Dipropylamino-5-isopropenylchroman

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Methyltriphenylphosphoniumbromide (0.62 g, 1.74 mmol) was dissolved in dry ethyl ether (20 ml) under nitrogen at ambient temperature and n-BuLi (0.7 ml, 2.5M, 1.74 mmol) was added and the solution was stirred for 4 hours. 3-Dipropylamino-5-acetylchroman (Example 7; 0.40 g, 1.45 mmol) was dissolved in dry diethyl ether (2.0 ml) and this solution was added to the previously formed Wittig-reagent.

Workup

  1. additionthis solution was added to the previously formed Wittig-reagent

Sources & evidence

ORD record
ord-bd94771345864b878983b06366730c7a
Source dataset
uspto-grants-1997_07
Patent number
US05646309

Reaction notes

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