Hydrochloric Acid → HCID 58706349, compound

HRID 1990853Notes

Reaction equation

HRID 1990853 reaction equation
[H-].[Na+].[CH3:3][SH:4].Br[C:6]1[C:13]([O:14][CH2:15][CH3:16])=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:17][CH2:18][CH3:19].Cl>CN(C=O)C>[CH2:18]([O:17][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:14][CH2:15][CH3:16])[C:6]=1[S:4][CH3:3])[CH:10]=[O:11])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 878MethanethiolHCID 24758Sodium hydrideHCID 59210363HCID 59210363, compound

Product 1

HCID 58706349HCID 58706349, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (2.62 g, 60.0 mmol, 2.0 equiv; 55% free-flowing powder moistened with oil) in DMF (50 mL) under Ar was added carefully methanethiol (2.88 g, 60.0 mmol, 2.0 equiv). After 15 min, a solution of 4-bromo-3,5-diethoxy-benzaldehyde (8.2 g, 30.0 mmol, 1.0 equiv; prepared according to S. P. Dudek, H. D. Sikes, C. E. D. Chidsey J. Am Chem. Soc. 2001, 123, 8033-8038) in DMF (30 mL) was added, and the reaction mixture stirred overnight. The mixture was acidified to pH 2 by addition of a solution of 1 M HCl and extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1) providing 6.9 g (96%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 6H), 2.50 (s, 3H), 4.18 (q, J=7.0 Hz, 4H), 7.02 (s, 2H), 9.88 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.66, 17.50, 64.88, 105.71, 122.00, 135.90, 159.54, 191.31. MS (ISP): 240.9 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvent removed by evaporation under reduced pressure
  4. customthe crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-c8925d45c4354bb7b77f2c582d342b19
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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