Tetrahydrofuran → HCID 14875419, compound

HRID 1757403Notes

Reaction equation

HRID 1757403 reaction equation
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].[CH3:8][S:9](Cl)(=[O:11])=[O:10].[O:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[S:9]([O:13][CH:17]1[CH:16]2[CH2:2][CH2:1][N:3]([CH2:14][CH2:15]2)[C:4]1=[CH2:5])(=[O:11])(=[O:10])[CH3:8]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 14875419HCID 14875419, compound

Procedure

Under a nitrogen atmosphere, in a round-bottom flask were placed 8 g (58 mmol) of the alcohol of Preparation A and 60 mL of tetrahydrofuran. To thesystem (cooled in an ice/acetone bath) was added 17.9 mL (128 mmol) of triethylamine followed by 5.13 mL (66 mmol) of methanesulfonyl Chloride over a period of 15 minutes. The mixture was gradually warmed to room temperature and stirred overnight. The reaction mixture was partitioned between 2N aqueous sodium hydroxide and chloroform, the layers were separated and the aqueous phase was extracted with chloroform. The combined chloroform fractions were dried (Na2SO4) and concentrated (rotary evaporator). The crude material was purified by flashcolumn chromatography (300 g of silica gel) using 1:9 methanol/chloroform as the eluant to obtain 5.3 g of the desired product. 1HNMR (CDCl3) delta 1.48 (m, 2H), 1.68 (m, 1H), 1.84 (m, 1H), 2.28 (m, 1H),2.76 (m, 1 H), 2.94 (m, 3H), 3.04 (s, 3H), 5.08 (d, 1H, J=5), 5.14 (s, 1H),5.24 (d, 1H, J=5).

Workup

  1. customUnder a nitrogen atmosphere, in a round-bottom flask were placed
  2. temperatureTo thesystem (cooled in an ice/acetone bath)
  3. customThe reaction mixture was partitioned between 2N aqueous sodium hydroxide and chloroform
  4. customthe layers were separated
  5. extractionthe aqueous phase was extracted with chloroform
  6. dry with materialThe combined chloroform fractions were dried (Na2SO4)
  7. concentrationconcentrated
  8. custom(rotary evaporator)
  9. customThe crude material was purified by flashcolumn chromatography (300 g of silica gel)

Sources & evidence

ORD record
ord-59b9f448a5cd43318fbeabd27d8f668e
Source dataset
uspto-grants-1995_08
Patent number
US05446050

Reaction notes

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