Hydrochloric Acid → 7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane

HRID 656044ノート

反応式

HRID 656044 の反応式
ClN1[C:6](=[O:7])[CH2:5]CC1=O.[CH:9]12[S:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][C:11](=[O:17])[CH2:10]2.[CH:18]([Mg]Br)(C)C.Cl>C1C=CC=CC=1.CCOCC>[CH3:18][CH:14]([CH:13]1[S:16][CH2:9][CH2:10][C:11]2([O:17][CH2:5][CH2:6][O:7]2)[CH2:12]1)[CH3:15]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 2750548-Thiabicyclo(3.2.1)octan-3-oneHCID 178418365HCID 178418365、化合物

生成物 1

HCID 593327327-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane収率 65.3%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒

実験手順

N-Chlorosuccinimide (14.0 g, 104.9 mmol) was added in three portions with stirring over 15 min to a cooled (0° C.) solution of 8-thiabicyclo[3.2.1]octan-3-one (16.0 g, 99.9 mmol) in dry benzene (400 mL) under nitrogen. The mixture was stirred for a further 2.5 h and was then filtered. The filtrate was added dropwise with stirring under nitrogen to a cooled (0° C.) solution of isopropylmagnesium bromide (from isopropyl bromide (28.3 g, 229.7 mmol), magnesium (5.7 g, 234.7 mmol) and CuI (1.52 g, 7.9 mmol)) in dry ether (300 mL). The mixture was stirred for a further 15 h and cold (0° C.), dilute hydrochloric acid was added cautiously. The organic layer was separated and washed successively with water, saturated aqueous sodium bicarbonate, and finally with water again. The dried (Na2SO4) ether-benzene solution was evaporated, giving 13.2 g of the title compound.

後処理

  1. stirringThe mixture was stirred for a further 2.5 h
  2. filtrationwas then filtered
  3. additionThe filtrate was added dropwise
  4. stirringwith stirring under nitrogen to
  5. stirringThe mixture was stirred for a further 15 h
  6. customThe organic layer was separated
  7. washwashed successively with water, saturated aqueous sodium bicarbonate
  8. dry with materialThe dried (Na2SO4) ether-benzene solution
  9. customwas evaporated

出典と根拠

ORDレコード
ord-b38c29a8b1ff41b5925e7ba996d83f2d
出典データセット
uspto-grants-2011_12
特許番号
US08071584B2

反応ノート

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