Toluene → HCID 70818548, compound

HRID 590983Notes

Reaction equation

HRID 590983 reaction equation
C([Li])CCC.[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[N:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[S:19][CH:20]=3)=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7]1.[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH:28]=[O:29].C1(C)C=CC=CC=1>O1CCCC1.O>[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[N:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[S:19][C:20]=3[CH:28]([OH:29])[C:27]([O:31][CH2:32][CH3:33])=[O:30])=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 70818685HCID 70818685, compoundHCID 178418339Butyllithium

Product 1

HCID 70818548HCID 70818548, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Butyl lithium (1.6M, 930 μL, 1.5 mmol) was added at −78° C. to a solution of 4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-phenyl-1,3-thiazole (9c) (330 mg, 1.12 mmol) in anhydrous tetrahydrofuran (10 mL). After 20 minutes, ethyl glyoxylate 50% in toluene (400 μL, 2 mmol) was added at −78° C. and the mixture was stirred for 2 hours, hydrolyzed with water and concentrated in vacuo. The residue was diluted with ethyl acetate (20 mL) and the organic layer was washed with water (10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired alcohol (9d) as a white solid (130 mg, 0.33 mmol, 29%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate (20 mL)
  3. washthe organic layer was washed with water (10 mL), brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-6770edb496f349e685037ffe1de23958
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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