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Phenylacetylene → Benzyl 2-benzyloxy-4-phenylethynyl-benzoate

HRID 322935
ノート
印刷プレビュー

反応式

HRID 322935 の反応式
[CH2:1]([O:8][C:9]1[CH:24]=[C:23](I)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([C:32]#[CH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Br.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([C:33]#[C:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 10821PhenylacetyleneHCID 10599389Benzyl 2-benzyloxy-4-iodobenzoate

生成物 1

HCID 10598112Benzyl 2-benzyloxy-4-phenylethynyl-benzoate収率 27.9%

試薬・触媒・溶媒 3

HCID 24593copper(I) bromide触媒HCID 178418397HCID 178418397、化合物触媒
HCID 8471
Triethylamine
溶媒

実験手順

Benzyl 2-benzyloxy-4-iodobenzoate (7.6 g) is added to triethylamine (120 mL) followed by phenylacetylene (2.94 g) then tetrakis(triphenylphosphine)palladium(0) (0.664 g) and copper (I) bromide (0.248 g). The resulting mixture is stirred at room temperature for 3 hours. The triethylamine is distilled off and the residue partitioned between ether (600 mL) and saturated aqueous ammonium chloride solution. The organic phase is dried over magnesium sulphate and evaporated. The residue is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (5:1 v/v). Fractions homogeneous in the required product are combined and evaporated to give benzyl 2-benzyloxy-4-phenylethynyl-benzoate (2 g) as a cream solid, m.p. 98-100° C.

後処理

  1. distillationThe triethylamine is distilled off
  2. customthe residue partitioned between ether (600 mL) and saturated aqueous ammonium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated
  5. customThe residue is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (5:1 v/v)
  6. customevaporated

出典と根拠

ORDレコード
ord-01ddd84156a7448b9f22bb951797c3bf
出典データセット
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06211234B1

反応ノート

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