N-Methoxy-N-methylacetamide → 1-(2,2-Dimethyl-2,4-dihydro-1,3-benzodioxin-6-yl)ethan-1-one

HRID 14453

반응식

HRID 14453 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[O:8][CH2:7][C:6]=2[CH:13]=1.C([Li])CCC.CN(OC)[C:21](=[O:23])[CH3:22]>C1COCC1.C(OCC)(=O)C>[C:21]([C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[O:8][CH2:7][C:6]=2[CH:13]=1)(=[O:23])[CH3:22]

참가 물질

6

반응물 3

HCID 537505N-Methoxy-N-methylacetamideHCID 145203386-Bromo-2,2-dimethyl-4H-benzo[d][1,3]dioxineHCID 178418339Butyllithium

생성물 1

HCID 218806101-(2,2-Dimethyl-2,4-dihydro-1,3-benzodioxin-6-yl)ethan-1-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To the product of step (a) (110 g, 0.46 mol) in 1.0 L of THF at −78° C. was added 236 mL (0.51 mol) of 2.14 M n-butyllithium in hexanes via a dropping funnel. After 30 minutes, N-methyl-N-methoxy acetamide (71 g, 0.69 mol, available from TCI) was added. After 2 hours, the reaction mixture was quenched with water, diluted with 2.0 L of 1.0 M aqueous phosphate buffer (pH=7.0) and extracted once with diethyl ether. The diethyl ether phase was washed once with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a light orange oil. The oil was dissolved in a minimum volume of ethyl acetate, diluted with hexanes, and to give the title compound as a crystalline solid.

후처리

  1. waitAfter 2 hours
  2. customthe reaction mixture was quenched with water
  3. additiondiluted with 2.0 L of 1.0 M aqueous phosphate buffer (pH=7.0)
  4. extractionextracted once with diethyl ether
  5. washThe diethyl ether phase was washed once with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a light orange oil

출처 및 근거

ORD 기록
ord-a9155af1242d4cf29799e396a83d0c1a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732441B2

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