Acetic Acid → HCID 58504106, compound

HRID 2407667Notes

Reaction equation

HRID 2407667 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=O)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH2:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:27])=[CH:24][C:23]=1[O:38][CH3:39].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>C(#N)C>[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH2:29][CH:30]2[CH2:31][CH2:32][N:33]([CH2:12][C:9]3[S:10][CH:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=3)[CH2:34][CH2:35]2)=[O:27])=[CH:24][C:23]=1[O:38][CH3:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 50094674-Phenylthiophene-2-carbaldehydeHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 66989233HCID 66989233, compound

Product 1

HCID 58504106HCID 58504106, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-phenylthiophene-2-carbaldehyde (0.074 g) and the compound prepared in Example 11 (0.075 g) and acetic acid (0.023 mL) in acetonitrile (1 mL) was stirred at room temperature for 30 minutes. Tetramethylammonium triacetoxyborohydride (0.156 g) was added and the reaction was stirred for 18 hours. The mixture was partitioned between a saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=9:1) to obtain the title compound (0.066 g) having the following physical data.

Workup

  1. customThe mixture was partitioned between a saturated aqueous sodium bicarbonate solution and ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=9:1)

Sources & evidence

ORD record
ord-b0ab0b2f58ab42099595294d7f3bc0ce
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…