Thionyl Chloride → 5-(Chloromethyl)-2,3-dihydro-1h-indene

HRID 468499ノート

反応式

HRID 468499 の反応式
S(Cl)([Cl:3])=O.[CH2:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14]O)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1>C(Cl)(Cl)Cl>[Cl:3][CH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[CH2:5][CH2:6][CH2:7]2

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 330183(2,3-dihydro-1H-inden-5-yl)methanol

生成物 1

HCID 2331495-(Chloromethyl)-2,3-dihydro-1h-indene収率 99%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Thionyl chloride (120 ml, 1.65 mol) was added drop-wise to a rapidly stirred mixture of (2,3-dihydro-1H-inden-5-yl)methanol (81.4 g, 0.55 mol) in chloroform (500 ml) at 0° C. After the addition was complete, the resulting mixture was allowed to warm to room temperature and the stifling was continued for an additional 12 h. The chloroform was evaporated under reduced pressure to give a residue, that was purified by column chromatography (petroleum ether:ethyl acetate=15:1) to afford 5-(chloromethyl)-2,3-dihydro-1H-indene (90.5 g, 99%). NMR (300 MHz, CDCl3) δ 2.06-2.19 (m, 4H), 2.93 (t, J=7.5, 4H), 4.54 (s, 2H), 7.15-7.31 (m, 3H).

後処理

  1. additionAfter the addition
  2. customThe chloroform was evaporated under reduced pressure
  3. customto give a residue, that
  4. customwas purified by column chromatography (petroleum ether:ethyl acetate=15:1)

出典と根拠

ORDレコード
ord-a13f5ab62d7346b689200027c1973b07
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

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