Ethyl Acetate → 3-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL

HRID 593363ノート

反応式

HRID 593363 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([O:11]C(=O)C)[CH2:7][CH2:8][C:9]=2[CH:10]=1.[OH-].[Na+].CCCCCCC.C(OCC)(=O)C>CO.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([OH:11])[CH2:7][CH2:8][C:9]=2[CH:10]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 14798Sodium HydroxideHCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

生成物 1

HCID 580828163-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL収率 91.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of acetic acid 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl ester (1.57 g, 7.42 mmol) in methanol (35.7 ml) was treated with 1M sodium hydroxide (8.9 ml). The mixture was stirred at room temperature for 1.5 hours. The reaction was followed by TLC (silica gel, heptane: ethyl acetate=1:1; UV detection 254 nm). After completion, the reaction mixture was treated with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulphate, then evaporated leaving a dark red liquid (1.15 g, 91%) which crystallised on standing. Following NMR the product was pure enough for the next step of the synthesis; (calculated) C8H8ClNO [169.61]; (found) [M+H]+=170.

後処理

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated

出典と根拠

ORDレコード
ord-0fd45fee51bb4036abcab90002729c7a
出典データセット
uspto-grants-2016_01
特許番号
US09242943B2

反応ノート

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