Nitrogen → 2-Decyl-2,3-dihydrothieno[3,4-b][1,4]dioxine

HRID 10610Notes

Reaction equation

HRID 10610 reaction equation
[CH3:1][O:2][C:3]1[C:7]([O:8][CH3:9])=[CH:6][S:5][CH:4]=1.C1(C)C=CC=CC=1.[CH2:17](O)[C@@H:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]CC.N#N>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>[CH2:17]([CH:1]1[O:2][C:3]2=[CH:4][S:5][CH:6]=[C:7]2[O:8][CH2:9]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 947NitrogenHCID 1140TolueneHCID 2733663(S)-1,2-DodecanediolHCID 36135013,4-Dimethoxythiophene

Product 1

HCID 98569932-Decyl-2,3-dihydrothieno[3,4-b][1,4]dioxineYield 68.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,4-dimethoxythiophene (1.90 g), toluene (30 ml), (S)-1,2-dodecanediol (2.50 g) and p-toluenesulfonic acid monohydrate (100 mg) was heated at 95° C., continuously leading a N2-stream over the solution. After 24 h the reaction mixture was poured into ethyl acetate, washed with NaHCO3 and the organic phase was concentrated. Subsequent filtration over SiO2 using n-hexane/CH2Cl2 (98/2) as eluant resulted in pure product (2.40 g).

Workup

  1. washwashed with NaHCO3
  2. concentrationthe organic phase was concentrated
  3. filtrationSubsequent filtration over SiO2

Sources & evidence

ORD record
ord-38c21bccac1c466a9310412c0c189a9d
Source dataset
uspto-grants-2006_08
Patent number
US07094865B2

Reaction notes

Loading…