Hydrochloric Acid → Methyl (1,2-benzoxazol-3-yl)acetate

HRID 1533013Notes

Reaction equation

HRID 1533013 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[N:2]1.[CH3:14]COCC.Cl>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3017292-(1,2-Benzoxazol-3-yl)acetic acid

Product 1

HCID 2763403Methyl (1,2-benzoxazol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,2-benzisoxazole-3-acetic acid (prepared according to G. Casini et al, J. Het. Chem. 6, 1969, 279) (18 g), ether saturated with dry HCl (150 ml) and methanol (200 ml) was stirred for 2 h at room temperature. Removal of the volatiles in vacuo gave methyl 1 ,2-benzisoxazole-3-acetate (17 g) as an oil. The oil was dissolved in tetrahydrofuran (100 ml) and added dropwise to a suspension of lithium aluminium hydride (6 g) in tetrahydrofuran (200 ml) at 0-10° C. followed by stirring for 30 min at 15° C. Usual work-up gave 2-(1 ,2-benzisoxazol-3-yl)ethanol (13 g) as an oil.

Workup

  1. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-d617c80cd00c42ca844004d2d4805f0a
Source dataset
uspto-grants-2001_03
Patent number
US06207677B1

Reaction notes

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