Sodium hydride → HCID 69067306, compound

HRID 1987822Notes

Reaction equation

HRID 1987822 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[O:8]=[C:9]1[C@H:13](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:12][CH2:11][O:10]1>C1COCC1>[OH:5][CH2:4][CH2:3][CH2:2][S:1][C@H:13]1[CH2:12][CH2:11][O:10][C:9]1=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 882113-MercaptopropanolHCID 86607006HCID 86607006, compound

Product 1

HCID 69067306HCID 69067306, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-mercaptopropan-1-ol (360 mg, 3.90 mmol) in THF (8 mL) cooled to 0° C. was treated with 60% NaH (86 mg, 2.15 mmol). After warming to room temperature and stirring for 30 minutes, a solution of (R)-toluene-4-sulfonic acid 2-oxotetrahydrofuran-3-yl ester (500 mg, 1.95 mmol) in THF (2 mL) was added. After stirring at room temperature for 60 hours, the reaction mixture was quenched with saturated NaHCO3 and diluted with EtOAc. The organic layer was washed with saturated NH4Cl, saturated NaHCO3, saturated NaCl, dried over Na2SO4 and concentrated under reduced pressure. The residue was chromatographed (2:1 EtOAc/hexanes) to provide the product as colorless oil (155 mg, 45%).

Workup

  1. stirringAfter stirring at room temperature for 60 hours
  2. customthe reaction mixture was quenched with saturated NaHCO3
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with saturated NH4Cl, saturated NaHCO3, saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (2:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-20fe5f904f17471584e390be09c04229
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

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