5-[(tert-Butyldiphenylsilyloxy)methyl]-5-[(tetradecanoyloxy)methyl]-tetrahydro-2-furanone → 5-[(Tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanone

HRID 363497ノート

反応式

HRID 363497 の反応式
[Si]([O:18][CH2:19][C:20]1([CH2:26][O:27][C:28](=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[O:24][C:23](=[O:25])[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:28]([O:27][CH2:26][C:20]1([CH2:19][OH:18])[O:24][C:23](=[O:25])[CH2:22][CH2:21]1)(=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

参加物

3

反応物 1

HCID 108412125-[(tert-Butyldiphenylsilyloxy)methyl]-5-[(tetradecanoyloxy)methyl]-tetrahydro-2-furanone

生成物 1

HCID 107844975-[(Tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanone収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 3d (0.118 g, 0.2 mmol) in THF (3 mL) at room temperature was stirred with a solution of n-tetrabutylammonium fluoride in THF (1M, 0.3 mL) for 40 min. The solution was evaporated under vacuum, dissolved in EtOAc (20 mL), dried (Na2SO4) and concentrated. The residue obtained was purified by flash column chromatography over silica gel using hexane:EtOAc (7:3) as eluant to give 3e (0.051 g, 72%) as a white solid; mp 65°-66° C. (EtOAc/hexane); IR (KBr) 3448.1, 1763.2, 1728.1 cm-1 ; 1H NMR (CDCl3) δ 0.88 (distorted t, 3 H, CH3), 1.30 (m, 20 H, CH3 (CH2)10CH2CH2CO); 1.60 (m, 2 H, CH3 (CH2)10CH2CH2CO), 2.00-2.12 (m, 2 H, H-4a), 2.20-2.30 (m, 2 H, H-4b), 2.33 (t, J=7.6 Hz, 2 H, CH3 (CH2)10CH2CH2CO), 2.45 (t, J=6.4 Hz, 1 H, OH), 2.65 (m, 2 H, H-3), 3.60 (dd, J=12.1, 5.9 Hz, 1 H, CHHOH), 3.75 (dd, J=12.1, 6.1 Hz, CHHOH), 4.10 (d, J=12.0 Hz, 1 H, CHHOCO), 4.30 (d, J=12.0 Hz, 1 H, CHHOCO); 13C NMR δ 14.09, 22.65, 24.81, 25.47, 28.79, 29.07, 29.19, 29.32, 29.41, 29.56, 29.60, 31.89, 34.03, 64.82, 65.45, 86.02, 173.48, 176.47; FAB MS (m/z, relative intensity) 357 (MH+, 100), 211 (C13H27CO+, 35). Anal. Calcd for C20H36O5 : C,67.37; H,10.18. Found: C,67.30; H,10.17.

後処理

  1. customThe solution was evaporated under vacuum
  2. dissolutiondissolved in EtOAc (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customwas purified by flash column chromatography over silica gel

出典と根拠

ORDレコード
ord-ab954ab3b50a452db972e67f33be0aa2
出典データセット
uspto-grants-1999_02
特許番号
US05874464

反応ノート

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