Triphenylphosphine → 3-[2(E)-(Quinolin-2-yl)ethenyl]benzyl chloride

HRID 866030Notes

Reaction equation

HRID 866030 reaction equation
[Cl:1]N1C(=O)CCC1=O.[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1/[CH:19]=[CH:20]/[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1/[CH:19]=[CH:20]/[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][Cl:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 701100023-[2(E)-(Quinolin-2-yl)ethenyl]benzyl alcohol

Product 1

HCID 199590993-[2(E)-(Quinolin-2-yl)ethenyl]benzyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid N-chlorosuccinimide (0.76 g 5.72 mmol) is added in portions over 5 minutes to a stirred solution of 3-[2(E)-(quinolin-2-yl)ethenyl]benzyl alcohol (1.14 g, 4.58 mmol) and triphenylphosphine (1.50 g, 5.72 mmol) in dichloromethane (100 ml) at 0°-5° C. The mixture is stirred for a further 2 hours at 0°-5° C. then evaporated and the residue chromatographed on silica in ethyl acetate-hexane (1:3).

Workup

  1. customthen evaporated
  2. customthe residue chromatographed on silica in ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-689c3c750d6d4c7da7c935aa93102517
Source dataset
uspto-grants-1996_10
Patent number
US05569764

Reaction notes

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