Potassium tert-butoxide → tert-butyldimethyl((3R,3aS,6aR)-6-methylene hexahydrofuro[3,2-b]furan-3-yloxy)silane

HRID 2168175ノート

反応式

HRID 2168175 の反応式
[CH3:1]C(C)([O-])C.[K+].[Si:7]([O:14][C@H:15]1[C@H:19]2[O:20][CH2:21][C:22](=O)[C@H:18]2[O:17][CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.O>[C:10]([Si:7]([CH3:8])([CH3:9])[O:14][C@@H:15]1[CH2:16][O:17][C@@H:18]2[C:22](=[CH2:1])[CH2:21][O:20][C@H:19]12)([CH3:11])([CH3:12])[CH3:13]

参加物

6

反応物 2

HCID 23665647Potassium tert-butoxideHCID 67049238(3aS,6R,6aS)-6-(tert-butyldimethylsilyloxy)tetrahydrofuro[3,2-b]furan-3(2H)-one

生成物 1

HCID 67049508tert-butyldimethyl((3R,3aS,6aR)-6-methylene hexahydrofuro[3,2-b]furan-3-yloxy)silane収率 234.7%

試薬・触媒・溶媒 3

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A stirred suspension of methyltriphenylphosphonium bromide (1.84 g, 5.16 mmol) and potassium tert-butoxide (578 mg, 5.16 mmol) in tetrahydrofuran (15 mL) was heated at reflux under an atmosphere of argon for 3 hours then allowed to cool to ambient temperature. A solution of ketone (87) (888 mg, 3.44 mmol) in tetrahydrofuran (7.5 mL) was added then heating at reflux continued for 2.25 hours. The mixture was diluted with water (30 mL) then the product extracted into diethyl ether (2×30 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and reduced in vacuo to leave residue (2.07 g). Flash chromatography over silica, eluting with ethyl acetate:heptane mixtures 0:100 to 15:85 gave alkene (88) as a colourless oil (799 mg, 91%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of argon for 3 hours
  3. temperaturethen heating
  4. temperatureat reflux
  5. extractionthe product extracted into diethyl ether (2×30 mL)
  6. washThe combined organic layers were washed with brine (25 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-2846e54726a94f90886273653e67f231
出典データセット
uspto-grants-2015_06
特許番号
US09045492B2

反応ノート

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