Triphenylphosphine → 2-(4-Chloromethylphenoxy)methylquinoline

HRID 1655047Notes

Reaction equation

HRID 1655047 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[CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]O)=[CH:23][CH:22]=1.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[CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][Cl:1])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 287755064-(Quinolin-2-ylmethoxy)benzyl alcohol

Product 1

HCID 147741632-(4-Chloromethylphenoxy)methylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid N-chlorosuccinimide (16.69 g) was added in portions to a stirred solution of 4-(quinolin-2-ylmethoxy)benzyl alcohol (26.58 g) and triphenylphosphine (32.89 g) in dichloromethane (600 ml) at 0°-5° C. The mixture was stirred for a further 1.5 hours at 0°-5° C. and then purified rapidly by pouring the mixture onto flash silica and eluting with petroleum spirit 40°-60° C.-diethyl ether (2:1) under vacuum.

Workup

  1. custompurified rapidly
  2. additionby pouring the mixture onto flash silica
  3. washeluting with petroleum spirit 40°-60° C.-diethyl ether (2:1) under vacuum

Sources & evidence

ORD record
ord-a2fa5b2a4a524557ad73c9137f624997
Source dataset
uspto-grants-1995_04
Patent number
US05410061

Reaction notes

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