Tetrahydrofuran → HCID 22606928, compound

HRID 2307551Notes

Reaction equation

HRID 2307551 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[CH2:28][OH:29])[CH2:6][S:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=O)=[CH:16][C:15]=2[CH3:24])[CH:11]=[CH:12][CH:13]=1.[CH2:30]([Mg]Br)[CH3:31].[Cl-].[NH4+].[CH2:36]1COC[CH2:37]1>>[CH2:36]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([S:7][CH2:6][C:5]3[CH:25]=[CH:26][C:27]([CH2:28][OH:29])=[C:3]([CH2:2][OH:1])[CH:4]=3)[CH:9]=2)=[C:15]([CH3:24])[CH:16]=1)([OH:22])[CH2:30][CH3:31])[CH3:37]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 69928469HCID 69928469, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 22606928HCID 22606928, compound

Procedure

130 mg (0.3 mmol) of methyl 3′-(3,4-bis-hydroxymethyl-benzylsulphanyl)-2-methylbiphenyl-4-carboxylate are dissolved in 10 mL of anhydrous THF and 0.7 mL (2 mmol) of an ethylmagnesium bromide solution (3M) are then added. The reaction medium is stirred for 1 h and then treated with ammonium chloride solution. After extraction with ethyl acetate, the organic phases are combined, dried and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica. A colourless oil is obtained (m=105 mg, Y=81%).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by chromatography on a column of silica
  5. customA colourless oil is obtained (m=105 mg, Y=81%)

Sources & evidence

ORD record
ord-1b44928b8e4a453fb8b9cb690ff6a8cc
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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