HCID 11369822, compound → HCID 11243225, compound

HRID 1989823Notes

Reaction equation

HRID 1989823 reaction equation
[Li][CH2:2]CCC.[Br:6][C:7]1[C:8]([O:19][CH3:20])=[CH:9][C:10]([Cl:18])=[C:11]([C:13]([CH3:17])([CH3:16])[CH:14]=O)[CH:12]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:6][C:7]1[CH:12]=[C:11]([C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:2])[C:10]([Cl:18])=[CH:9][C:8]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 11369822HCID 11369822, compoundHCID 178418339Butyllithium

Product 1

HCID 11243225HCID 11243225, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of methyltriphenylphosphonium bromide (11.4 g, 0.032 mol) in dry THF (100 mL) was cooled to 0° C. under argon. n-BuLi (2.5M, 12 mL, 0.030 mol) was added slowly. The suspension became more homogenous. The resulting clear orange solution of the ylide was stirred for another 15 min at 0° C. 2-(5-Bromo-2-chloro-4-methoxy-phenyl)-2-methyl-propionaldehyde (7.8 g, 0.027 mol) was dissolved in dry THF (50 mL) and added to ylide-solution. The mixture was stirred for 3 h/25° C. and the resulting suspension was quenched with MeOH (10 mL). The solvent was removed under reduced pressure and the crude product was purified by flash chromatography using n-heptane as eluent. Yield: 3.92 g (50%). GCMS: >99%

Workup

  1. additionadded to ylide-solution
  2. stirringThe mixture was stirred for 3 h/25° C.
  3. customthe resulting suspension was quenched with MeOH (10 mL)
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-927cb8bdb22340b694c0138a24b810a7
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

Loading…