2-Methyl-3-butyn-2-ol → 4-(1,1-Dimethyl-2-propynyloxy)bromobenzene

HRID 892569ノート

反応式

HRID 892569 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH:8]=[C:7](C3C=CC=C[N+]=3[O-])[C:6]=2[CH:20]=1.ClC1C=CC(C2C=CC=CC=2)=CN=1.CC(O)(C#C)C.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:11][C:9]([CH3:12])([O:10][C:5]1[CH:6]=[CH:20][C:2]([Br:1])=[CH:3][CH:4]=1)[C:8]#[CH:7]

参加物

7

反応物 5

HCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27628682-Chloro-5-phenylpyridineHCID 536691392-(6-bromo-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide

生成物 1

HCID 540101944-(1,1-Dimethyl-2-propynyloxy)bromobenzene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The 6-bromo-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran used as the starting material was prepared as follows: (A) 69.2 g of p-bromophenol and 33.6 g of 2-methylbut-3-yn-2-ol were dissolved in 600 ml of dichloromethane and 75 ml of diethyl azodicarboxylate were added. 126 g of triphenylphosphine were added portionwise and the mixture was stirred overnight. The mixture was washed with dilute hydrochloric acid and 2M sodium hydroxide solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:10) for the elution. There was obtained an oil which was distilled to give 14.4 g of 4-(1,1-dimethyl-2-propynyloxy)bromobenzene of boiling point 96°-106° C./1 mmHg. (B) In an analogous manner to that described in Example 6(A), from 4-(1,1-dimethyl-2-propynyloxy)bromobenzene and 2-iodopyridine there was obtained 6-bromo-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran.

後処理

  1. customwas prepared
  2. washThe mixture was washed with dilute hydrochloric acid and 2M sodium hydroxide solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution
  7. customThere was obtained an oil which
  8. distillationwas distilled

出典と根拠

ORDレコード
ord-f90d11b9f12b4a738628f048bcdcb403
出典データセット
uspto-grants-1992_06
特許番号
US05118694

反応ノート

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