Water → HCID 66699467, compound

HRID 1818470Notes

Reaction equation

HRID 1818470 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([SH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].I[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(=O)CC>[C:12]([C:3]1[CH:4]=[CH:5][C:6]([S:11][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C@H:23]([O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[C:24]3[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=3)[C:27]#[N:28])=[CH:21][CH:22]=2)=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneHCID 57884505(S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

Product 1

HCID 66699467HCID 66699467, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Stir a mixture of 1-(2-Hydroxy-4-mercapto-3-propyl-phenyl)-ethanone (250 mg, 1.18 mmol), (S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (515 mg, 1.18 mmol) and cesium carbonate (769 mg, 2.36 mmol) in 2-butanone (10 ml) at room temperature under argon for 24 hours. Pour the mixture into water (85 ml) and extract with ethyl acetate (3×25 ml). Combine the organic extracts and wash with water, brine, then dry over sodium sulfate, filter and concentrate. Purify the crude product via silica chromatography eluting with 1:4 ethyl acetate:hexanes to give the title compound (325 mg, 53%). MS (m/z) 514 (M−H).

Workup

  1. extractionextract with ethyl acetate (3×25 ml)
  2. washCombine the organic extracts and wash with water, brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude product via silica chromatography
  7. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-e5e6b3081c88481390825b43fa6746a4
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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