Sulfuric Acid → HCID 11565859, compound

HRID 1162534Notes

Reaction equation

HRID 1162534 reaction equation
[CH2:1]([C@@H:7]1[CH2:9][O:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O1CCCC1.[CH2:15]([Mg]Cl)[CH3:16].[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].S(=O)(=O)(O)O>O1CCCC1.[Cl-].[Na+].C(OCC)(=O)C>[CH3:26][C:25]1[CH:27]=[CH:28][C:22]([S:19]([O:8][C@@H:7]([CH2:9][CH2:15][CH3:16])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chlorideHCID 1620686(2R)-2-HexyloxiraneHCID 178420661HCID 178420661, compound

Product 1

HCID 11565859HCID 11565859, compoundYield 103.8%

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-25 °C

Procedure

Under an argon atmosphere, cuprous chloride (4.6 g) was added to a solution of (2R)-2-hexyloxirane (300 g) in tetrahydrofuran (642 mL), and then ethylmagnesium chloride tetrahydrofuran solution (2.1 mol/L, 1309 g) was added dropwise at −40 to −20° C. (inner temperature). The reaction mixture was stirred at −30 to −20° C. (inner temperature) for about 30 minutes, and then tosyl chloride (491 g) was added, and the mixture was stirred at 0-20° C. (inner temperature) for about 4 hours. To the reaction mixture was then added 10 v/v % sulfuric acid (conc. sulfuric acid:water=65 mL:650 mL), aqueous sodium chloride (13.6 g) solution (272 mL) and ethyl acetate (1.5 L) for extraction. The resulting organic layer was washed with (1) a solution of sodium chloride (32 g) in water (636 mL), (2) a mixture of a solution of potassium carbonate (73 g) in water (730 mg) and a saturated brine (200 mL), and (3) a saturated brine (600 mL) in order, and then concentrated to give the title compound (758.7 g; yield 89%).

Workup

  1. stirringthe mixture was stirred at 0-20° C. (inner temperature) for about 4 hours
  2. extractionfor extraction
  3. washThe resulting organic layer was washed with (1) a solution of sodium chloride (32 g) in water (636 mL), (2)
  4. additiona mixture of a solution of potassium carbonate (73 g) in water (730 mg)
  5. concentrationa saturated brine (200 mL), and (3) a saturated brine (600 mL) in order, and then concentrated

Sources & evidence

ORD record
ord-51a5bb2ef960448283443422c6852b8a
Source dataset
uspto-grants-2010_10
Patent number
US07820715B2

Reaction notes

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