Thiophene → HCID 525987, compound

HRID 589267Notes

Reaction equation

HRID 589267 reaction equation
[Li]CCCC.[S:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH2:24]([C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

5

Reactant 3

HCID 8030ThiopheneHCID 8208Myristyl bromideHCID 178418339Butyllithium

Product 1

HCID 525987HCID 525987, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (1.6 M, 48 mL, 76 mmol) was added dropwise to a solution of thiophene (7.0 g, 83 mmol) in THF (70 mL) at −78° C. and stirred for 45 min. Tetradecyl bromide (23 mL, 76 mmol) in THF (25 mL) was added dropwise to the resultant suspension and then gradually warmed to room temperature and stirred for 18 h. The reaction mixture was quenched with water (60 mL) and extracted with diethyl ether (2×100 mL). The combined organic extracts were dried over MgSO4 and concentrated to give brown oil (20.7 g, 97%), which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.10 (d, 1H, J=5.2 Hz), 6.91 (dd, 1H, J=5.7, 4.4 Hz), 6.77 (d, 1H, J=3.2 Hz), 2.82 (t, 2H, J=7.6 Hz), 1.68 (q, 2H, J=6.8 Hz), 1.50-1.20 (m, 22H), 0.88 (t, 3H, J=6.8 Hz).

Workup

  1. stirringstirred for 18 h
  2. customThe reaction mixture was quenched with water (60 mL)
  3. extractionextracted with diethyl ether (2×100 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-497a7110f0124a4d9795a0b1cf7d1318
Source dataset
uspto-grants-2016_01
Patent number
US09231215B2

Reaction notes

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