Water → HCID 53840232, compound

HRID 6212Notes

Reaction equation

HRID 6212 reaction equation
[Br-].[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:12]=1.[Li]CCCC.[OH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][N:49]1[C:58]2[C:53](=[CH:54][C:55]([CH:59]=[CH:60][CH:61]=O)=[CH:56][CH:57]=2)[CH2:52][CH2:51][CH2:50]1.O>C1(C)C=CC=CC=1>[OH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][N:49]1[C:58]2[C:53](=[CH:54][C:55]([CH:59]=[CH:60][CH:61]=[CH:17][C:14]3[CH:13]=[CH:12][C:11]([C:3]4[O:2][C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[N:4]=4)=[CH:16][CH:15]=3)=[CH:56][CH:57]=2)[CH2:52][CH2:51][CH2:50]1

Participants

6

Reactant 4

HCID 962WaterHCID 54151230HCID 54151230, compoundHCID 867444264-(Benzoxazol-2-yl)tolyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 53840232HCID 53840232, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred mixture of 110 g (0.2 mole) of 4-(benzoxazol-2-yl)tolyltriphenylphosphonium bromide in toluene is added dropwise 0.2 mole of n-BuLi at room temperature. After 2 hours a solution of 28.7 g (0.1 mole) of 3-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)acrolein in toluene is added dropwise to the mixture, and the reaction is stirred for 18 hours at room temperature. Water is added, and the solids are isolated by vacuum filtration, washed with 60% ethanol/water, and dried under vacuum. The product is purified by recrystallization from benzene.

Workup

  1. customthe solids are isolated by vacuum filtration
  2. washwashed with 60% ethanol/water
  3. customdried under vacuum
  4. customThe product is purified by recrystallization from benzene

Sources & evidence

ORD record
ord-56e0c8bc731e4aa9a568d920148f452a
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Reaction notes

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