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Sodium hydride → HCID 58046042, compound

HRID 657975
Notes
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Reaction equation

HRID 657975 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:7]=1.Br[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[F:12][S:8]([F:13])([F:9])([F:10])([F:11])[C:6]1[CH:5]=[C:4]([C:14](=[O:16])[CH3:15])[CH:3]=[C:2]([O:1][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 58136805HCID 58136805, compound

Product 1

HCID 58046042HCID 58046042, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Procedure

1-[3-Hydroxy-5-(pentafluorosulfanyl)phenyl]ethanone (O3.050; 700 mg) and 2-(2-bromo-ethoxy)tetrahydropyran (670 mg) were dissolved in DMF (15 ml), and sodium hydride (77 mg) was added. After stirring at RT for 2 h, the mixture was heated to 50° C. for 4 h and left to stand over the weekend. Then the DMF was drawn off and the residue was taken up in EA. The EA phase was washed with water, dried, filtered and concentrated. The crude product was purified using silica gel (100 g, n-heptane/EA 4:1). 813 mg of the title compound were obtained.

Workup

  1. temperaturethe mixture was heated to 50° C. for 4 h
  2. waitleft
  3. washThe EA phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-cb14b5183aa14abea0603e8ad9f55509
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08076336B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes