Sodium hydride → HCID 59506307, compound

HRID 1098766Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:10][C:11]1[S:15][C:14]([C:16]2[CH:17]=[C:18]([C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][C:21]=2F)=[CH:13][CH:12]=1>CS(C)=O>[Cl:10][C:11]1[S:15][C:14]([C:16]2[CH:17]=[C:18]([C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][C:21]=2[O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 10 °C

Procedure

Tetrahydro-pyran-4-ol (1.01 g, 5.01 mmol) was added dropwise at 0° C. to a suspension of sodium hydride (200 mg, 5.01 mmol) in DMSO (10 ml). After stirring for 30 min at 10° C., a solution of the product obtained from step 1 (850 mg, 3.34 mmol) in DMSO (2 ml) was added dropwise and stirring was continued for 1 h at RT. The reaction was quenched with ice/water (50 ml). Ethyl acetate (50 ml) was added and the aqueous phase was extrated with ethyl acetate (2×30 ml). The combined organic phases were washed with brine (2×50 ml), dried over sodium sulphate, filtered, and evaporated. The product was obtained in quantitative yield and used in the next step without further purification.

Workup

stirringstirring
waitwas continued for 1 h at RT
customThe reaction was quenched with ice/water (50 ml)
additionEthyl acetate (50 ml) was added
washThe combined organic phases were washed with brine (2×50 ml)
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated
customThe product was obtained in quantitative yield
customused in the next step without further purification

Sources & evidence

ORD record: ord-25e2cd43ac6d4e4eb38225dcade8adb3
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143242B2

Reaction notes

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