Hydrochloric Acid → HCID 178419611, compound

HRID 231558Notes

Reaction equation

HRID 231558 reaction equation
C([Li])CCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7]1.[Br-:15].[Mg+2:16].[Br-].C[Si](C)(C)N(CC#CCOC)[Si](C)(C)C.Cl>Cl[Ni]Cl.CCOCC>[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[Mg:16][Br:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7221Benzo(B)ThiopheneHCID 82241Magnesium BromideHCID 13161121N,N-bis(trimethylsilyl)-4-methoxy-2-butynylamineHCID 178418339Butyllithium

Product 1

HCID 178419611HCID 178419611, compound

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2-Benzothiophenylmagnesium bromide was prepared by adding butyllithium (5.1 ml. 15.8 mM) to benzothiophene (1.7 g, 12.7 mM) in a 3-necked, 100 ml flask with septum, stir bar, thermometer, and nitrogen inlet, in the presence of ether (15 ml), allowing reaction to reflux about 15 minutes, and then cooling to 0° C. in ice. Magnesium bromide etherate (12.7 mM) was added all at once and was allowed to warm to 20° C. over about 15 minutes. Then NiCl2 (dppp) (30 mg) was added and, following the procedure described in Example 2, III (12.7 mM) was added and stirred overnight to produce the crude silylate product, the reaction being complete by G C analysis after that time. 1M ethanolic hydrochloride (0.9 equivalent), was added to the etheral solution to yield 1.7 g (72%) of hydrochloride salt as a pale yellow solid, Mp 235° C. (dec) (EtoH).

Workup

  1. customreaction
  2. temperatureto reflux about 15 minutes
  3. temperatureto warm to 20° C. over about 15 minutes
  4. additionwas added
  5. stirringstirred overnight
  6. customto produce the crude silylate product

Sources & evidence

ORD record
ord-bc075e3dbe014a0ab69b722b1c1864ef
Source dataset
uspto-grants-1989_07
Patent number
US04847288

Reaction notes

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