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Sodium Iodide → 4-Methylpentyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 57219
Notes
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Reaction equation

HRID 57219 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].Br[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C)C=O.CCOC(C)=O.[Cl-].[Na+].O.O>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 69385Pentane, 1-bromo-4-methyl-HCID 1151755-(Tetradecyloxy)-2-furoic acid2×

Product 1

HCID 668698124-Methylpentyl 5-(tetradecyloxy)furan-2-carboxylateYield 62.2%

Reagents, catalysts & solvents 4

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

To a vigorously stirred suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (0.162 g, 0.5 mmol) in 10 mL of N,N-dimethylformamide was added 1-bromo-4-methylpentane (0.247 g, 1.5 mmol), cesium carbonate (0.243 g, 0.75 mmol) and sodium iodide (˜20 mg). The suspension appeared to go into solution briefly, and then a very finely dispersed white precipitate was observed. The reaction was allowed to stir for 12 hrs at which time HPLC analysis of the reaction solution indicated complete conversion of TOFA to a less polar product. The suspension was diluted with EtOAc (40 mL), brine (20 mL) and water (20 mL). The phases were separated and the organic phase was washed with water (20 mL) and brine (20 mL) and then dried and concentrated. The resulting crude material was purified by flash chromatography eluting with 0-20% EtOAc in hexanes to yield 0.127 g (62%) of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.15 (d, 1H), 5.30 (d, 1H), 4.22 (t, 2H), 4.10 (t, 2H), 1.18-1.80 (m, 29H), 0.89 (t, 9H).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water (20 mL) and brine (20 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crude material was purified by flash chromatography
  6. washeluting with 0-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-06c8b30c5e0f4d0090984b9d5fe78529
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434718B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes