(+-)-2-Butanol → HCID 86747417, compound

HRID 327016Notes

Reaction equation

HRID 327016 reaction equation
[CH2:1]([P:3](Cl)([CH2:5][O:6][S:7]([C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])(=[O:9])=[O:8])=[O:4])[CH3:2].[CH:19]([OH:23])([CH2:21][CH3:22])[CH3:20].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([P:3]([CH2:5][O:6][S:7]([C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])(=[O:9])=[O:8])(=[O:4])[O:23][CH:19]([CH2:21][CH3:22])[CH3:20])[CH3:2]

Participants

6

Reactant 3

HCID 6568(+-)-2-ButanolHCID 8471TriethylamineHCID 18981624HCID 18981624, compound

Product 1

HCID 86747417HCID 86747417, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.83 g of P-ethyl[[(2-chloro-6-methylphenyl)sulfonyloxy]-methyl]phosphinoyl chloride (Example 51) and 0.2 g of 4-dimethylaminopyridine (DMAP) in 15 ml of methylene chloride at 10° C. was added dropwise over 10 minutes a solution of 1.52 g of sec-butanol and 2.32 g of triethylamine in 8 ml of methylene chloride. After 1 hour, the cooling bath was removed and the reaction was warmed to room temperature and stirred an additional two hours. The reaction mixture was diluted with ethyl acetate, 20 ml, ether, 50 ml, and water, 60 ml, and the organic phase was separated, washed with an additional 50 ml of water, dried with magnesium sulfate, filtered and concentrated. The resulting oil was dissolved in 4 ml of methylene chloride and flash chromatographed on Merck silica gel using blends of ethyl acetate and hexanes. Similar fractions were combined to yield 3.2 g of desired product as a tan oil.

Workup

  1. customthe cooling bath was removed
  2. additionThe reaction mixture was diluted with ethyl acetate, 20 ml, ether, 50 ml, and water, 60 ml
  3. customthe organic phase was separated
  4. washwashed with an additional 50 ml of water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe resulting oil was dissolved in 4 ml of methylene chloride
  9. customflash chromatographed on Merck silica gel using blends of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-af8fcefc21964ae58816c491de52c5a5
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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