Toluene → 2-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzenemethanol

HRID 258468Notes

Reaction equation

HRID 258468 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:11]1(C)[CH:16]=C[CH:14]=[CH:13][CH:12]=1.[Br-].[Cl:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26]([CH2:30][O:31][C:32]3[CH:33]=[C:34]([CH2:38][P+](C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:35]=[CH:36][CH:37]=3)=[N:27]2)=[CH:22][CH:21]=1.[CH2:58]1[CH2:62][O:61][CH2:60][CH2:59]1>>[Cl:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26]([CH2:30][O:31][C:32]3[CH:33]=[C:34]([CH:38]=[CH:14][CH2:13][C:12]4[CH:11]=[CH:16][CH:60]=[CH:59][C:58]=4[CH2:62][OH:61])[CH:35]=[CH:36][CH:37]=3)=[N:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 8028Tetrahydrofuran2×HCID 3251421Potassium bis(trimethylsilyl)amideHCID 88417068((3-((7-Chloro-2-quinolinyl)methoxy)phenyl)methyl)triphenylphosphonium bromide

Product 1

HCID 541888982-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzenemethanolYield 90%

Conditions

Temperature
0 °C

Procedure

At -10° C., a solution of 0.65M KHMDS (potassium hexamethyldisilazide) in toluene (21 mL, 13.65 mmol) was added dropwise to a suspension of the phosphonium salt of Step 4 (8.457 g, 13.53 mmol) in THF (70 mL) and the mixture was stirred at 0° C. for 30 min. At -78° C., a solution of 1H-3-hydroxy-3,4-dihydrobenzo(c)pyran (1.141 g, 7.60 mmol) in THF (14 mL) was added slowly. The mixture was allowed to warm to r.t. and was stirred for a further 3 hours. Aqueous NH4OAc 25% was added and the products were extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica using EtOAc:toluene 10:90 and 15:85. The title compound (2.84 g, 90% yield) was obtained as a cis:trans mixture and was used as such for the next step.

Workup

  1. temperatureto warm to r.t.
  2. stirringwas stirred for a further 3 hours
  3. extractionthe products were extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-01b1917eec9c467abf3b68d31a739227
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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