Stannane, [2,2'-bithiophen]-5-yltributyl- → 4-Formyl-5-hydroxymethyl-2,2':5', 2"-terthiophene

HRID 1599512ノート

反応式

HRID 1599512 の反応式
C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1)CCC.[CH:24]([C:26]1[CH:30]=[C:29](I)[S:28][C:27]=1[CH2:32][OH:33])=[O:25]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O1CCCC1>[CH:24]([C:26]1[CH:30]=[C:29]([C:6]2[S:10][C:9]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][CH:7]=2)[S:28][C:27]=1[CH2:32][OH:33])=[O:25]

参加物

5

反応物 2

HCID 11201877Stannane, [2,2'-bithiophen]-5-yltributyl-HCID 189288892-(Hydroxymethyl)-5-iodothiophene-3-carbaldehyde

生成物 1

HCID 573213644-Formyl-5-hydroxymethyl-2,2':5', 2"-terthiophene収率 38%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a two-necked round bottomed flask was added 5-tributylstannyl-2,2'-bithiophene (2.04 g), bis(triphenylphosphine)palladium (II) chloride (0.19 g), 3-formyl-2-hydroxymethyl-5-iodo-thiophene (1.0 g) and tetrahydrofuran (20 ml). The reaction mixture was refluxed for 16 hours. Extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was separated by silica gel chromatography, eluted with n-hexane/ethyl acetate (9:1→1:1 gradient) to give brownish solid product (0.43 g, 38%), melting point 108°-110° C.

後処理

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. extractionExtracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was separated by silica gel chromatography
  7. washeluted with n-hexane/ethyl acetate (9:1→1:1 gradient)

出典と根拠

ORDレコード
ord-39c20772fcec42f3b22ab542dcb257ec
出典データセット
uspto-grants-1998_04
特許番号
US05741811

反応ノート

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