Tetrahydrofuran → HCID 17984299, compound

HRID 1181031Notes

Reaction equation

HRID 1181031 reaction equation
CO[C:3](=O)[CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:12]=[N:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)[S:8][C:9]=1[CH3:10].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:33]CC1>>[CH3:10][C:9]1[S:8][C:7]([C:11]2[CH:12]=[N:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)=[N:6][C:5]=1[CH:4]([OH:33])[CH3:3]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 58978986HCID 58978986, compound

Product 1

HCID 17984299HCID 17984299, compound

Procedure

A solution of [5-methyl-2-(6-phenyl-pyridin-3-yl)-thiazol-4-yl]-acetic acid methyl ester (6.0 g, 18.5 mmol) in THF (500 mL) was added dropwise to a suspension of LAH (0.90 g, 22.2 mmol) in THF (300 mL) at −78° C. After the addition was completed, the reaction mixture was allowed to warm to ambient temperature, cooled to −20° C., and quenched sequentially with H2O (1.1 mL), 15% NaOH (1.1 mL), and H2O (3.3 mL). The mixture was filtered through Celite, and the filtrated was concentrated to give the title compound as an oil that was used directly in the next step.

Workup

  1. additionAfter the addition
  2. temperaturecooled to −20° C.
  3. customquenched sequentially with H2O (1.1 mL), 15% NaOH (1.1 mL), and H2O (3.3 mL)
  4. filtrationThe mixture was filtered through Celite
  5. concentrationthe filtrated was concentrated

Sources & evidence

ORD record
ord-39eb4893887649dd82131ddca17a9675
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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