4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 69217389, compound

HRID 272732

Reaction equation

HRID 272732 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[CH3:11][C:12]1[N:13]=[CH:14][S:15][C:16]=1[CH2:17][CH2:18]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][CH2:17][C:16]2[S:15][CH:14]=[N:13][C:12]=2[CH3:11])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 11776TriphenylphosphineHCID 2622344-Bromo-2-methoxyphenolHCID 5387121Dibenzyl azodicarboxylate

Product 1

HCID 69217389HCID 69217389, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromo-2-methoxy-phenol (50.8 mg, 0.25 mmol), 2-(4-methyl-thiazol-5-yl)-ethanol (49.5 mg, 0.25 mmol) and polymer-supported triphenyl phosphine (250 mg, 0.75 mmol) in THF (2.5 mL) was stirred at room temperature for 20 minutes. DBAD (86.3 mg, 0.375 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was filtered through Celite®, rinsing with THF and methanol. The filtrate was concentrated, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel (10 to 20% ethyl acetate in hexane) to give the title compound. MS (ESI) m/e 329 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 8.82 (s, 1H), 7.12 (d, J=2.4 Hz, 1H), 7.03 (dd, J=8.5, 2.4 Hz, 1H), 6.91 (d, J=8.5 Hz, 1H), 4.10 (t, J=6.4 Hz, 2H), 3.77 (s, 3H), 3.20 (t, J=6.4 Hz, 2H), 2.35 (s, 3H).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washrinsing with THF and methanol
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by column chromatography on silica gel (10 to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ed514b5f95dd4b72bf78e549e5649397
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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