Sodium hydride → HCID 67707349, compound

HRID 54799Notes

Reaction equation

HRID 54799 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[CH:7][CH:6]=1.Br[C:14]1[CH:15]=[C:16]([CH2:21][OH:22])[S:17](=[O:20])(=[O:19])[CH:18]=1>O1CCCC1.O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][CH:14]2[CH2:18][S:17](=[O:20])(=[O:19])[CH:16]([CH2:21][OH:22])[CH2:15]2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 18923992HCID 18923992, compound

Product 1

HCID 67707349HCID 67707349, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a 0° C. slurry, under argon, of 0.502 g of sodium hydride (60% oil dispersion) in 9 ml of dry tetrahydrofuran is added, dropwise over 5 minutes, 1.69 mi of p-methoxy-α-toluenethiol in 9 ml of dry tetrahydrofuran. The reaction is warmed to room temperature for 30 minutes, recooled to 0° C. and a solution of 2.31 g of product from Example 176 in 10 ml of dry tetrahydrofuran is added. The reaction mixture is allowed to warm to room temperature and stirred overnight. The mixture is diluted with 100 ml of water and extracted with diethyl ether. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo to give an oil. The oil is purified by chromatography (silica gel: 0-90% ethyl acetate/hexane) to give 3.0 g of the desired product (1:1 mixture of isomers).

Workup

  1. customrecooled to 0° C.
  2. temperatureto warm to room temperature
  3. extractionextracted with diethyl ether
  4. washThe organic layer is washed with saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customThe oil is purified by chromatography (silica gel: 0-90% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-08f024e616524314828b5db0ab878611
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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