Thiazole → HCID 58415351, compound

HRID 2075206Notes

Reaction equation

HRID 2075206 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH:20]=[O:21])=[CH:19][C:14]=2[CH:13]=[CH:12]1>C1COCC1>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH:20]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[OH:21])=[CH:19][C:14]=2[CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 27738751-Benzofuran-5-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 58415351HCID 58415351, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon at −78° C., a mixture of thiazole (1.13 g, 13.2 mmol) in THF (50 mL) was dropwise treated with 2.5M n-BuLi (1.05 equiv., 5.04 mL, in hexanes) over a period of 10 min and stirred for 45 min. The resulting yellow mixture was treated dropwise with a solution of benzofuran-5-carbaldehyde (1.76 g, 12.0 mmol) in THF (10 mL). Cooling was removed after addition. When the mixture reached room temperature, it was treated with EtOAc, washed with 1M aqueous HCl and brine, dried over MgSO4, and evaporated, to give benzofuran-5-yl(thiazol-2-yl)methanol as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.71-7.75 (m, 2H), 7.64 (d, J=2.2 Hz, 1H), 7.50 (d, J=8.6 Hz, 1H), 7.39 (dd, J=8.6, 1.7 Hz, 1H), 7.29 (d, J=3.1 Hz, 1H), 6.76-6.75 (m, 1H), 6.17 (s, 1H).

Workup

  1. temperatureCooling
  2. customwas removed
  3. additionafter addition
  4. customreached room temperature
  5. additionit was treated with EtOAc
  6. washwashed with 1M aqueous HCl and brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-23755378c04748fda146d13e33b6e1c1
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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