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2-Chlormethyl-8-(1,1-dimethylethyl)-1,4-dioxaspiro(4.5)decan → 8-t-Butyl-2-(phthalimidomethyl)-1,4-dioxaspiro(4,5)decane

HRID 1449498
ノート
印刷プレビュー

反応式

HRID 1449498 の反応式
[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13]Cl)[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13][N:21]3[C:20](=[O:22])[C:19]4=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]4[C:17]3=[O:27])[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 143262942-Chlormethyl-8-(1,1-dimethylethyl)-1,4-dioxaspiro(4.5)decanHCID 24194345Phthalimide potassium salt2 回

生成物 1

HCID 199636648-t-Butyl-2-(phthalimidomethyl)-1,4-dioxaspiro(4,5)decane収率 101.4%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 8-t-butyl-2-chloromethyl-1,4-dioxaspiro(4,5)decane (10 g, 40 mmol) (prepared as described in EP 281842; see also the references cited in this document for-related compounds), potassium phthalimide (8.9 g, 48 mmol) and a catalytic amount of tetra-n-butyl ammonium iodide in DMF (80 ml) were heated to 120° C. for 3 hours. Additional potassium phthalimide (2.8 g, 16 mmol) was then added and heating was continued for 6 hours. The solvent was then evaporated in vacuo and toluene (150 ml) was added. After filtration from insoluble material the organic phase was washed two times with brine (100 ml), dried (MgSO4) and evaporated in vacuo. The resulting residue (22 g) was purified by flash chromatography on silica (toluene/ethylacetate 3:1) yielding the title compound as light yellow crystals (14.5 g, Fp. 97°-115° C.).

後処理

  1. customprepared
  2. temperatureheating
  3. customThe solvent was then evaporated in vacuo and toluene (150 ml)
  4. additionwas added
  5. filtrationAfter filtration from insoluble material the organic phase
  6. washwas washed two times with brine (100 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe resulting residue (22 g) was purified by flash chromatography on silica (toluene/ethylacetate 3:1)

出典と根拠

ORDレコード
ord-f51cbe3ec0384ca0868a54b86681f1cb
出典データセット
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05599818

反応ノート

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