Water → HCID 57637382, compound

HRID 2078745Notes

Reaction equation

HRID 2078745 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:11]([O:8][CH2:7][C:4]1[S:5][CH:6]=[C:2]([Br:1])[CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2795484(4-Bromo-2-thienyl)methanol

Product 1

HCID 57637382HCID 57637382, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To (4-bromo-thiophen-2-yl)-methanol (18.8 g, 97.4 mmol, Intermediate (85)] in tetrahydrofuran (200 mL) was added sodium hydride (3.9 g, 97.4 mmol) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 30 minutes. Tetrabutylammonium iodide (3.6 g, 9.7 mmol) was added followed by benzyl bromide (11.6 mL, 97.4 mmol). The mixture was stirred at room temperature for 1 hour. Water was added. The resulting mixture was extracted with diethyl ether. The ether layer was dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (n-heptane/ethyl acetate, 90/10 as eluant) to provide 2-benzyloxymethyl-4-bromo-thiophene [29.2 g, Intermediate (86)] (quantitative) as a yellow oil. LC/MS: 282.96 (M+H), RT=3.68 minutes.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionThe resulting mixture was extracted with diethyl ether
  3. dry with materialThe ether layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed through silica gel (n-heptane/ethyl acetate, 90/10 as eluant)

Sources & evidence

ORD record
ord-237643cc5b1848e4addb05b4c031cde7
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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