Dimethyl Sulfide → (3,4-Dihydro-2H-1,4-benzoxazin-8-yl)methanol

HRID 1898170Notes

Reaction equation

HRID 1898170 reaction equation
O=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12](O)=[O:13])[C:5]=2[O:4][CH2:3]1.S(C)C.[NH4+].[Cl-]>C1COCC1>[O:4]1[C:5]2[C:11]([CH2:12][OH:13])=[CH:10][CH:9]=[CH:8][C:6]=2[NH:7][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 25517Ammonium ChlorideHCID 183549413-Oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid

Product 1

HCID 53414296(3,4-Dihydro-2H-1,4-benzoxazin-8-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1.51 g, 7.8 mmol) in anhydrous THF (10 mL) was added BH3.Me2S (2 M in THF, 10 mL, 20 mmol) dropwise under nitrogen at 0° C. The resulted mixture was allowed to rise to r.t., and the reaction was continued to be carried out at this temperature overnight. Then, saturated aqueous NH4Cl (30 mL) was added in, and the resulted mixture was extracted with EtOAc (200 mL×2). The combined organic layers were washed with saturated aqueous NaHCO3 solution (30 mL), brine (30 mL), dried (Na2SO4) and filtered before it was concentrated under reduced pressure. The resulted crude product (3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)methanol, which was utilized in the following step without further purification. MS m/z: 166.2 (M+H)+.

Workup

  1. additionwas added BH3
  2. customat 0° C
  3. customto rise to r.t.
  4. customto be carried out at this temperature overnight
  5. extractionwas extracted with EtOAc (200 mL×2)
  6. washThe combined organic layers were washed with saturated aqueous NaHCO3 solution (30 mL), brine (30 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered before it
  9. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-18d8d599baf34037b230543b9a226415
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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