Hydrochloric Acid → HCID 59457470, compound

HRID 1710738Notes

Reaction equation

HRID 1710738 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:18](OC)=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.CO.[BH4-].[Li+].Cl.[OH-].[Na+]>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[O:13][C:14]([CH2:18][OH:19])=[C:15]([CH3:17])[N:16]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 59457502HCID 59457502, compound

Product 1

HCID 59457470HCID 59457470, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-oxazole-5-carboxylate ax60 (390 mg, 1.26 mmol, 1 eq) and methanol (165 μl, 4.08 mmol, 1.8 eq) in tetrahydrofuran (13 ml) is treated with lithium borohydride (49 mg, 2.27 mmol, 1.8 eq) and the mixture is stirred at 70° C. for 1 h. After cooling back to 0° C., the mixture is treated dropwise with 1 N aqueous hydrochloric acid (1 ml). The mixture is then made basic (pH 10) with 2 N aqueous sodium hydroxide and extracted with ethyl acetate. The organic phase is then dried over magnesium sulfate and concentrated to give 330 mg of {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-oxazol-5-yl}methanol ax61 as a yellow solid.

Workup

  1. temperatureAfter cooling back to 0° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is then dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fcc240a344cd4cd49aa63da4ff58c4c4
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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