4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 68327671, compound

HRID 707630Notes

Reaction equation

HRID 707630 reaction equation
[CH3:1][C:2]([O-])(C)[CH3:3].[K+].C1COCC1.[OH:12][CH2:13][CH2:14][C:15]1[S:19][CH:18]=[N:17][C:16]=1[CH3:20].C(Br)C=C>O>[CH2:3]([O:12][CH2:13][CH2:14][C:15]1[S:19][CH:18]=[N:17][C:16]=1[CH3:20])[CH:2]=[CH2:1]

Participants

6

Reactant 4

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxide

Product 1

HCID 68327671HCID 68327671, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

An oven-dried 100 mL round bottom flask was charged with t-BuOK (20.8 mmol), dry THF (25 mL), purged with argon and cooled to 0° C. in an ice bath. 5-(2-Hydroxyethyl)-4-methylthiazole (16 mmol) was then added dropwise to the solution and the reaction stirred at 0° C. for 1 h under argon. Allyl bromide (20.8 mmol) was added dropwise, and the solution was warmed to R.T. and allowed to stir for 20 h under argon. Deionized water (4 mL) was then added and the reaction stirred for 10 min. All liquid were then removed in vacuo and the residue redissolved in ethyl acetate (50 mL). The organic phase was washed three times with water (20 mL), dried over Na2SO4, filtered over Celite, and then concentrated in vacuo to yield a yellow oil (96%). 1HNMR (400 MHz, CDCl3): δ=8.52 (s, 1H), 5.89 (m, 1H), 5.23 (dd, 1H, 3JHHtrans=17.4 Hz, 2JHHgems=1.8 Hz), 5.13 (dd, 1H, 3JHHcis=10.3 Hz, 2JHHgems=1.6 Hz), 3.96 (dt, 2H, 3JHH=5.7 Hz, 4JHH=1.4 Hz), 3.57 (t, 2H, 3JHH=6.9 Hz), 2.99 (t, 2H, 3JHH=6.9 Hz), 2.37 (s, 3H) ppm. 13CNMR (400 MHz, CDCl3): δ=149.6, 149.2, 134.5, 127.9, 17.0, 71.9, 70.0, 27.0, 14.9 ppm. HRMS-ESI: Calculated [M+H]+: 184.0791. found: 184.0787.

Workup

  1. custompurged with argon
  2. temperaturethe solution was warmed to R.T.
  3. stirringto stir for 20 h under argon
  4. stirringthe reaction stirred for 10 min
  5. customAll liquid were then removed in vacuo
  6. dissolutionthe residue redissolved in ethyl acetate (50 mL)
  7. washThe organic phase was washed three times with water (20 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered over Celite
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9352eebfc2d47c7a1d9df1b6dea7511
Source dataset
uspto-grants-2015_11
Patent number
US09175026B2

Reaction notes

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