Diethyl fumarate → Trans 2,3-dicarboethoxy-1,2,3,4-tetrahydronaphthalene

HRID 901991Notes

Reaction equation

HRID 901991 reaction equation
[CH2:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4]S(=O)O1.[C:12]([O:21][CH2:22][CH3:23])(=[O:20])/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(C)C=CC=CC=1>[C:12]([C@H:13]1[C@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:1][C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:4]1)([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 638144Diethyl fumarateHCID 118298361,4-Dihydro-2,3-benzoxathiin-3-oxide

Product 1

HCID 12187587Trans 2,3-dicarboethoxy-1,2,3,4-tetrahydronaphthaleneYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 1,4-dihydro-2,3-benzoxathiin 3-oxide (2.0 g, 11.9 mmol) in toluene (20 mL) was added diethyl fumarate (3.9 mL, 23.8 mmol). Upon completion of addition, the reaction mixture was heated to 110° C. for 16 h under nitrogen. The solvent was removed under vacuum to yield a residue. The residue was purified by silica gel chromatography eluting with 10% ethyl acetate in hexane to yield the title compound (2.1 g, 64%). 13C NMR (400 MHz, CDCl3) δ 174.1, 133.7, 128.3, 126.1, 60.5, 42.3, 42.0, 31.6, 14.3, 14.0. 1H NMR (400 MHz, CDCl3) δ 7.04-7.15 (m, 4H), 4.18 (m, 4H), 3.12 (dd, J=2.6, 12.4 Hz, 2H), 2.87-3.03 (m, 4H), 1.27 (t, J=7.5 Hz, 6H). MS [M+Na]+, 299.

Workup

  1. additionUpon completion of addition
  2. customThe solvent was removed under vacuum
  3. customto yield a residue
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7d89a2aa67b3459c94138f5ad15923a8
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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