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

HRID 490992

反応式

HRID 490992 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a2edf8a96af45adb0600e1fa74cbeb1
出典データセット
uspto-grants-2009_05
特許番号
US07528253B2

関連ノート

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