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

HRID 869854

反応式

HRID 869854 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 stirring 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%). 1H 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-4a3756c987734f16ae59478bb5fb46b7
出典データセット
uspto-grants-2015_03
特許番号
US08969386B2

関連ノート

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