HCID 10503817, compound → HCID 54335570, compound

HRID 322888Notes

Reaction equation

HRID 322888 reaction equation
[CH2:1]([Li])CCC.[C:6]([C:9]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)=[CH:27][C:10]=1[O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=O)[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:12]([O:11][C:10]1[CH:27]=[C:28]([O:31][CH2:32][C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)[CH:29]=[CH:30][C:9]=1[C:6]([CH3:7])=[CH2:1])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 10503817HCID 10503817, compoundHCID 178418339Butyllithium

Product 1

HCID 54335570HCID 54335570, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of methyltriphenylphosphonium bromide (2.4 g) in tetrahydrofuran (50 mL) at ambient temperature is treated with a solution of butyllithium in hexanes (2.6 mL; 2.5 M). After two hours, the reaction mixture is treated with a solution of ethyl (RS)-4-[2-acetyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)-butanoate (1 g) in tetrahydrofuran (2 mL) and stirred for a further two hours. It is then partitioned between hydrochloric acid (50 mL; 1 N) and ethyl acetate (100 mL). The organic layer is washed with water (50 mL), dried over magnesium sulphate, filtered and concentrated in vacuo. The residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:9 v/v) to give ethyl (RS)-4-(2-methylphenyl)-4-[2-(propen-2-yl)-5-(3-thienylmethoxy)phenoxyl]butanoate (0.7 g), in the form of a colourless oil.

Workup

  1. customIt is then partitioned between hydrochloric acid (50 mL; 1 N) and ethyl acetate (100 mL)
  2. washThe organic layer is washed with water (50 mL)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washeluting with a mixture of ethyl acetate and cyclohexane (1:9 v/v)

Sources & evidence

ORD record
ord-9daf047bc4a442dbbeb0bb49cc38f596
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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