Acetaldehyde → 6,7-Dichloro-5-hydroxy-alpha-methylbenzo[b]thiophene-2-methanol

HRID 485919

反応式

HRID 485919 の反応式
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11].C([Li])CCC.C(Cl)(Cl)(Cl)Cl.C(=O)=O.[CH:26](=[O:28])[CH3:27].Cl>O1CCCC1>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[C:8]([CH:26]([CH3:27])[OH:28])[S:7][C:6]=2[C:10]=1[Cl:11]

参加物

7

反応物 5

HCID 177Acetaldehyde2 回HCID 313Hydrochloric AcidHCID 132899976,7-Dichloro-1-benzothiophene-5-olHCID 86602444Carbontetrachloride dry-iceHCID 178418339Butyllithium

生成物 1

HCID 134776546,7-Dichloro-5-hydroxy-alpha-methylbenzo[b]thiophene-2-methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 25 g of 6,7-dichloro-5-hydroxybenzo[b]thiophene in 145 ml of dried tetrahydrofuran at -25° to -30° is added 110 ml of 2.5M n-butyllithium maintaining a temperature below -21°. After the addition, the carbon tetrachloride-dry ice bath is replaced with an ice-water bath and the mixture is stirred at 0°-5° for 4 hrs. A solution of 7.5 ml of freshly distilled acetaldehyde in 10 ml tetrahydrofuran is added dropwise. An additional 2 ml of acetaldehyde is added and the solution is stirred for 1 hr. The solution is poured onto 500 ml of a cold 5% hydrochloric acid solution and the mixture is extracted with ethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and solvent is removed to give a solid. Recrystallization from ethyl acetate and hexane gives 20 g of 6,7-dichloro-5-hydroxy-α-methylbenzo[b]thiophene-2-methanol, mp 173°-174°.

後処理

  1. additionAfter the addition
  2. stirringthe solution is stirred for 1 hr
  3. extractionthe mixture is extracted with ethyl ether
  4. washThe ether extracts are washed
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customsolvent is removed
  8. customto give a solid
  9. customRecrystallization from ethyl acetate and hexane

出典と根拠

ORDレコード
ord-1d1fde232b8843a4b2aeeb6b7ae7ff7f
出典データセット
uspto-grants-1985_08
特許番号
US04537976

関連ノート

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