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

HRID 363497노트

반응식

HRID 363497 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab954ab3b50a452db972e67f33be0aa2
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874464

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