Sodium borohydride → HCID 13106143, compound

HRID 594211Notes

Reaction equation

HRID 594211 reaction equation
[O:1]([C:8]1[S:9][CH:10]=[C:11]([C:13](OC)=[O:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[O:1]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69084587Methyl 2-phenoxythiazole-4-carboxylate

Product 1

HCID 13106143HCID 13106143, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-phenoxythiazole-4-carboxylate (265 mg; 1.12 mmol) in anh. EtOH (6 ml) was treated at rt with NaBH4 (213 mg; 5.64 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 63 h. After concentration to dryness under reduced pressure, water was added, and the resulting mixture was extracted with DCM. The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=30/1) afforded (2-phenoxythiazol-4-yl)methanol as a colorless oil. LC-MS (conditions A): tR=0.58 min.; [M+H]+: 208.06 g/mol.

Workup

  1. concentrationAfter concentration to dryness under reduced pressure, water
  2. additionwas added
  3. extractionthe resulting mixture was extracted with DCM
  4. dry with materialThe organic layer was dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=30/1)

Sources & evidence

ORD record
ord-db09c8b4a36d43c48da17c1eff072b35
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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