Formaldehyde → HCID 21424986, compound

HRID 258873Notes

Reaction equation

HRID 258873 reaction equation
[C:1]([C:3]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[CH:4]=1)#[CH:2].C([Mg]Br)C.[CH2:23]=[O:24].[Cl-].[NH4+]>O1CCCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[S:7][C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=3[CH:4]=[C:3]([C:1]#[C:2][CH2:23][OH:24])[C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 21424956HCID 21424956, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 21424986HCID 21424986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 13.5 g of 10-ethynyl-8-chloro-dibenzo[ b,f] thiepin in 150 ml. of absolute tetrahydrofuran is treated dropwise at room temperature with 52 ml. of a 1-M solution of ethylmagnesium bromide solution in tetrahydrofuran. After stirring the mixture for an additional hour, 1.85 g of paraformaldehyde are pyrrolyzed and led through the mixture in gaseous form. The solution, having now warmed to about 50° C., is stirred for an additional 30 minutes and then poured onto a saturated, aqueous ammonium chloride solution. By extraction with benzene and subsequent chromatography on silica gel using benzene/methanol (20:1) as the eluant, there is obtained 3-(8-chloro-dibenzo[ b,f] thiepin-10-yl)-2-propyn-1-ol which melts at 111°-113° C. after recrystallization from ethyl acetate/petroleum ether.

Workup

  1. stirringis stirred for an additional 30 minutes
  2. extractionBy extraction with benzene and subsequent chromatography on silica gel

Sources & evidence

ORD record
ord-7136f37f2aac46ebb33791442308a37c
Source dataset
uspto-grants-1977_07
Patent number
US04035385

Reaction notes

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