diisopropyl (E)-4-(t-butyldimethylsilyloxy)but-1-enylphosphonate → diisopropyl (E)-4-hydroxybut-1-enylphosphonate

HRID 1708082

反応式

HRID 1708082 の反応式
[Si]([O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[P:13](=[O:22])([O:18][CH:19]([CH3:21])[CH3:20])[O:14][CH:15]([CH3:17])[CH3:16])(C(C)(C)C)(C)C>C(O)(=O)C.O>[OH:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[P:13](=[O:22])([O:14][CH:15]([CH3:17])[CH3:16])[O:18][CH:19]([CH3:21])[CH3:20]

参加物

3

反応物 1

HCID 10020796diisopropyl (E)-4-(t-butyldimethylsilyloxy)but-1-enylphosphonate

生成物 1

HCID 10399205diisopropyl (E)-4-hydroxybut-1-enylphosphonate収率 76%

試薬・触媒・溶媒 1

HCID 21899381Acetic acid--water (1/1)溶媒

実験手順

A solution of diisopropyl (E)-4-(t-butyldimethylsilyloxy)but-1-enylphosphonate (0.84 g, 2.40 mmol) in acetic acid-water (2:1) (10 ml) was stirred at 70° C. for 2 hr. The solvent was removed and the residue purified by column chromatography on silica gel eluting with acetone-hexane (1:1) to give diisopropyl (E)-4-hydroxybut-1-enylphosphonate as a gum (0.43 g, 76%); νmax (film) 3380, 2970, 1625, 1460, 1380, 1370, 1220 and 980 cm-1 ; δH (CDCl3) 1.32 (12H, dd, J 9 Hz and 6 Hz, CH(CH3)2), 1.85 (1H, br.s, OH), 2.50 (2H, m, CH2), 3.76 (2H, t, J 6 Hz, CH2O ), 4.69 (2H, m, CH(CH3)2), 5.80 (1H, dd, J 16 Hz and 18 Hz, PCH=CH) 6.75 (1H, ddt, J 7 Hz, 17 Hz and 22 Hz, PCH=CH); CIMS (isobutane) 237 (MH+).

後処理

  1. customThe solvent was removed
  2. customthe residue purified by column chromatography on silica gel eluting with acetone-hexane (1:1)

出典と根拠

ORDレコード
ord-9cacdb0520014e7890e297a598134479
出典データセット
uspto-grants-1994_10
特許番号
US05356886

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