Hexane → HCID 59560535, compound

HRID 1176183Notes

Reaction equation

HRID 1176183 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:7][N:8]([CH3:10])[CH3:9])[S:5][CH:6]=1.[CH:11]([O:14][B:15](OC(C)C)[O:16][CH:17]([CH3:19])[CH3:18])([CH3:13])[CH3:12].[Li]CCCC.CCCCCC>C1COCC1>[CH3:9][N:8]([CH2:7][C:4]1[S:5][CH:6]=[C:2]([B:15]([O:16][CH:17]([CH3:19])[CH3:18])[O:14][CH:11]([CH3:13])[CH3:12])[CH:3]=1)[CH3:10]

Participants

6

Reactant 4

HCID 8058HexaneHCID 21531Triisopropyl borateHCID 223495551-(4-Bromothiophen-2-yl)-N,N-dimethylmethanamineHCID 178418339Butyllithium

Product 1

HCID 59560535HCID 59560535, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(4-bromo-2-thienyl)-N,N-dimethylmethanamine (2.8 g, 12.8 mmol) in THF (130 mL) at −78° C. under N2 was added tri-isopropylborate (4.4 mL, 19.2 mmol). The reaction mixture was stirred briefly before nBuLi (12 mL of a 1.6 M hexane solution) was added dropwise via syringe. The reaction mixture then stirred for 6.5 h at −78° C. before being concentrated by rotary evaporation. The resulting white solid was used without further purification.

Workup

  1. additionwas added dropwise via syringe
  2. concentrationbefore being concentrated by rotary evaporation
  3. customThe resulting white solid was used without further purification

Sources & evidence

ORD record
ord-80cca4dac3e54285a11ed7e60fac83ce
Source dataset
uspto-grants-2010_11
Patent number
US07842803B2

Reaction notes

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