Triethylamine → HCID 178505302, compound

HRID 2417977Notes

Reaction equation

HRID 2417977 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[O:5]=[CH:6][C@@H:7]([CH2:9][OH:10])[OH:8].C(N(CC)CC)C.[S:18](Cl)([CH3:21])(=[O:20])=[O:19]>ClCCl>[CH2-:1][C:2]([CH3:4])=[O:3].[S:18]([O:5][CH2:6][C@H:7]([OH:8])[CH2:9][OH:10])([CH3:21])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178521098HCID 178521098, compound

Product 1

HCID 178505302HCID 178505302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2(S)-glycerol-2,3-acetonide (109 g), obtained from mannitol-1,2:5,6-diacetonide via D-glyceraldehyde acetonide using the method described by LeCocq et al., Biochem., 3, 976 (1964), in 1 L dry dichloromethane was cooled to -35° with stirring. Triethylamine (140 ml) was added followed by the dropwise addition of mesyl chloride (71 ml) over 10 minutes while maintaining the reaction between -35° and -25°. The cooling bath was removed and after 45 minutes, 250 ml 1N hydrochloric acid was added. The layers were separated and the dichloromethane solution was washed in turn with 250 ml portions of water (1×), 1N sodium hydroxide (1×) and water (1×). The aqueous layers were dried over sodium sulfate and evaporated to give 172.1 g of (2R)-3-mesyloxy-1,2-propanediol acetonide as a pale yellow oil.

Workup

  1. temperaturewhile maintaining
  2. customthe reaction between -35° and -25°
  3. customThe cooling bath was removed and after 45 minutes
  4. addition250 ml 1N hydrochloric acid was added
  5. customThe layers were separated
  6. washthe dichloromethane solution was washed in turn with 250 ml portions of water (1×), 1N sodium hydroxide (1×) and water (1×)
  7. dry with materialThe aqueous layers were dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-17496b13ed4646cf8d299d6ea26c4c4f
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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