Boron trifluoride etherate → 6-[2-(5-Ethoxycarbonyl-5-methyl-hexyl)-[1,3]dithian-2-yl)-2,2-dimethyl-hexanoic acid ethyl ester

HRID 48001

Reaktionsgleichung

Reaktionsgleichung von HRID 48001
[CH2:1]([O:3][C:4](=[O:26])[C:5]([CH3:25])([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:2].[CH2:27]([SH:31])[CH2:28][CH2:29][SH:30].B(F)(F)F.CCOCC>ClCCl>[CH2:1]([O:3][C:4](=[O:26])[C:5]([CH3:25])([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:22])[CH3:21])[S:31][CH2:27][CH2:28][CH2:29][S:30]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 117266597-Oxo-2,2,12,12-tetramethyltridecanedioic acid diethyl ester

Produkt 1

HCID 206312146-[2-(5-Ethoxycarbonyl-5-methyl-hexyl)-[1,3]dithian-2-yl)-2,2-dimethyl-hexanoic acid ethyl esterAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under N2 atmosphere, to a solution of 2,2,12,12-tetramethyl-7-oxo-tridecanedioic acid diethyl ester (1.0 g, 2.70 mmol) and 1,3-propanedithiol (361 mg, 361 μL, 3.24 mmol) in dichloromethane (20 mL; dried with Aluminum oxide, activated, neutral, Brockmann I) was added boron trifluoride diethyl etherate (100 μL) at rt. The reaction mixture was stirred for 3 h, diluted with dichloromethane (100 mL), and extracted with 5% NaOH solution (100 mL) and water (75 mL). The organic phase was dried over MgSO4, concentrated in vacuo, and dried in high vacuo to furnish 6-[2-(5-ethoxycarbonyl-5-methyl-hexyl)-[1,3]dithian-2-yl]-2,2-dimethyl-hexanoic acid ethyl ester (1.0 g, 80%) as a yellowish oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 4.11 (q, 4H, J=7.1), 2.79 (t, 4H, J=5.6), 1.94 (m, 2H), 1.84 (m, 4H), 1.54 (m, 4H), 1.39 (m, 4H), 1.24 (t, 6H, J=7.1), 1.30-1.20 (m, 4H), 1.16 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 178.08, 60.33, 53.32, 42.27,40.69, 38.28, 26.14, 25.67, 25.28, 24.71, 14.41. HRMS (LSIMS, nba): Calcd. for C24H45S2O4 (MH+): 461.2759, found 461.2774.

Aufarbeitung

  1. extractionextracted with 5% NaOH solution (100 mL) and water (75 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customdried in high vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72112f38218540238068e9663f779046
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699910B2

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