Diisobutylaluminum hydride → 6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 2261102Notes

Reaction equation

HRID 2261102 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1)=O.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 2974054Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Product 1

HCID 184524436-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-oneYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carboxylate (30 g, 0.145 mol) in dry CH2Cl2 (500 mL) was cooled to −78° C. and added DIBAL-H (51 g, 0.36 mol) over a period of 45 min and then stirred at the same temperature for 14 h. The reaction mixture was quenched with 1.5N HCl and filtered off the solid product. The solid compound was dried under vacuum to give 6-(hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one (18 g, 69%).

Workup

  1. customThe reaction mixture was quenched with 1.5N HCl
  2. filtrationfiltered off the solid product
  3. customThe solid compound was dried under vacuum

Sources & evidence

ORD record
ord-57293158f9874c6d96e052d3b9b1fa68
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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