Calcium Carbonate → HCID 59593883, compound

HRID 2262331Notes

Reaction equation

HRID 2262331 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][CH:11]=3)[S:8][CH:9]=[C:2]12.C(=O)([O-])[O-].[Ca+2]>CO>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:7]2[S:8][CH:9]=[C:2]3[C:3]=2[O:4][CH2:5][CH2:6][O:1]3)=[CH:15][CH:14]=1)#[CH:17]

Participants

4

Reactant 2

HCID 10112Calcium CarbonateHCID 59593876HCID 59593876, compound

Product 1

HCID 59593883HCID 59593883, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As shown in the following Reaction 4, 200 mg (0.63 mmol) of [4-(2,3-Dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-phenylethynyl]-trimethyl-silane obtained in C of Example 1-1 was melted in 5 mL of methyl alcohol, and 170 mg (1.27 mmol, 2 eq) of calcium carbonate was added thereto, and then the reaction product was stirred for 12 hours. Next, the reaction solution was extracted with 10 mL of methylene chloride 1 time. The organic solvent layer was dehydrated with magnesium sulfate, filtered, and then distilled under reduced pressure. The compound distilled under reduced pressure was purified with a column chromatography (mobile phase volume ratio: methylene chloride:n-hexane=2:3) to obtain 140 mg of 5-(4-Ethynyl-phenyl)-2,3-dihydro-thieno[3,4-b][1,4]dioxine with the yield of 93%. NMR data of the obtained compound is as follows. [1H NMR (400 MHz, CDCl3): δ 3.10 (s, 1H), 4.23-4.26 (m, 2H), 4.29-4.32 (m, 2H), 6.33 (s, 1H), 7.46 (d, 2H), 7.67 (d, 2H)].

Workup

  1. customobtained in C of Example 1-1
  2. extractionNext, the reaction solution was extracted with 10 mL of methylene chloride 1 time
  3. filtrationfiltered
  4. distillationdistilled under reduced pressure
  5. distillationThe compound distilled under reduced pressure
  6. customwas purified with a column chromatography (mobile phase volume ratio: methylene chloride:n-hexane=2:3)

Sources & evidence

ORD record
ord-a09b81fb019942d0b3e8b98a0891da6c
Source dataset
uspto-grants-2010_12
Patent number
US07850872B2

Reaction notes

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