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

HRID 363497Notes

Reaction equation

HRID 363497 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ab954ab3b50a452db972e67f33be0aa2
Source dataset
uspto-grants-1999_02
Patent number
US05874464

Reaction notes

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