Ethyl Acetate → (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 57211

Reaction equation

HRID 57211 reaction equation
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]1[O:33][C:34](=[O:38])[O:35][C:36]=1[CH3:37].CCOC(C)=O>CN(C=O)C>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:31][C:32]2[O:33][C:34](=[O:38])[O:35][C:36]=2[CH3:37])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1151755-(Tetradecyloxy)-2-furoic acidHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

Product 1

HCID 49869762(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(tetradecyloxy)furan-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, room temperature solution of 5-(tetradecyloxy)furan-2-carboxylic acid (0.228 g, 0.70 mmol) in DMF (4 mL) was added potassium carbonate (0.146 g, 1.05 mmol) and 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one (0.160 g, 0.84 mmol). The reaction vessel was capped and stirring was continued for 14 hrs at which time TLC ((20% EtOAc in Hexanes Rf=0.10 (SM) and 0.40 (Prod)) indicated complete consumption of the starting material. The reaction was quenched by the addition of water (5 mL), brine (5 mL) and EtOAc (30 mL). The biphasic mixture was transferred to a seperatory funnel and the organic phase was extracted 3 times with brine (3×10 mL). The organic phase was dried and concentrated to give a colourless oil. The resulting crude material was purified by flash chromatography eluting with 5-20% EtOAc in hexanes to yield a colourless syrup that solidified on standing. 1H NMR (400 MHz, DMSO-d6) δ: 7.2 (d, 1H), 5.6 (d, 1H), 5.1 (s, 2H), 4.1 (t, 2H), 2.18 (s, 3H), 1.6-1.8 (m, 2H), 1.3-1.4 (m, 2H), 1.23 (d, 6H), 1.2 (s, 20H), 0.85 (t, 3H).

Workup

  1. customThe reaction vessel was capped
  2. customconsumption of the starting material
  3. customThe reaction was quenched by the addition of water (5 mL), brine (5 mL) and EtOAc (30 mL)
  4. customThe biphasic mixture was transferred to a seperatory funnel
  5. extractionthe organic phase was extracted 3 times with brine (3×10 mL)
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. customto give a colourless oil
  9. customThe resulting crude material was purified by flash chromatography
  10. washeluting with 5-20% EtOAc in hexanes
  11. customto yield a colourless syrup that

Sources & evidence

ORD record
ord-925f62bc6a8d4fbf83dbe7638c1244f8
Source dataset
uspto-grants-2016_09
Patent number
US09434718B2

Linked notes

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