Toluene → HCID 70855539, compound

HRID 591002Notes

Reaction equation

HRID 591002 reaction equation
C([Li])CCC.[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[N:17]=[C:18]([CH3:21])[S:19][CH:20]=3)=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7]1.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[CH:23]=[O:24].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]([CH3:21])[S:19][C:20]=3[CH:23]([OH:24])[C:22]([O:26][CH2:27][CH3:28])=[O:25])=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 70818377HCID 70818377, compoundHCID 178418339Butyllithium

Product 1

HCID 70855539HCID 70855539, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, butyl lithium (1.6M, 840 μL, 1.34 mmol) was added at −78° C. to a solution of 4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-methyl-1,3-thiazole (13a) (260 mg, 1.12 mmol) in anhydrous tetrahydrofuran (5 mL). After 30 minutes, ethyl glyoxylate 50% in toluene (500 μL, 2.5 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 (13b) as a white solid (90 mg, 0.27 mmol, 24%).

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-d260d9e969224a7091c8c7741b9775ff
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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