HCID 53271813, compound → HCID 86680486, compound

HRID 2406452Notes

Reaction equation

HRID 2406452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH:13]=[O:14])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][CH2:16][Mg+].[Br-]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH:13]([OH:14])[CH2:15][CH3:16])=[N:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 53271813HCID 53271813, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 86680486HCID 86680486, compoundYield 73%

Procedure

Using 5-(4-fluorophenyl)thiazole-2-carbaldehyde (0.12 g, 0.58 mmol) and EtMgBr (0.577 mL, 1.73 mmol) and following the procedure described for example 7 and step 2, the crude compound was obtained and further purified by column chromatography (using 100-200μ silica gel and 38% ethyl acetate and hexane) to give 1-(5-(4-fluorophenyl)thiazol-2-yl)propan-1-ol as pale yellow liquid (0.1 g, 73% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.68-7.65 (m, 2H), 7.25 (t, 2H), 6.11 (d, 1H), 4.72-4.67 (m, 1H), 1.84 (m, 1H), 1.88-1.67 (m, 1H), 0.91 (t, 3H); LC-MS m/z calculated for [M+H]+ 238.06, found 238.5.

Workup

  1. customthe crude compound was obtained
  2. customfurther purified by column chromatography (using 100-200μ silica gel and 38% ethyl acetate and hexane)

Sources & evidence

ORD record
ord-a532ae896934439a84296a8f5d1b2651
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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