Tetrahydrofuran → HCID 68522216, compound

HRID 1990075Notes

Reaction equation

HRID 1990075 reaction equation
[Li].[C:2]([O:6][C:7](=[O:15])[NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1Br)([CH3:5])([CH3:4])[CH3:3].[CH3:16][Sn:17](Cl)([CH3:19])[CH3:18].[CH2:21]1[CH2:25]OC[CH2:22]1>>[C:2]([O:6][C:7](=[O:15])[NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[Sn:17]([CH2:19][CH2:22][CH2:21][CH3:25])([CH2:18][CH2:10][CH2:9][CH3:13])[CH2:16][CH2:3][CH2:2][CH3:4])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14016Trimethyltin chlorideHCID 3028194LithiumHCID 13164363tert-Butyl (2-bromothiophen-3-yl)carbamate

Product 1

HCID 68522216HCID 68522216, compound

Procedure

Add n-buthyl lithium (19.8 ml, 1.6 M/hexane) dropwise to a solution 2-Bromothiophen-3-yl-carbamic acid tert-butyl ester (4 g, 14.4 mmol) in anhydrous THF (35 ml) at −78° C. Stir the mixture for 45 minutes and add trimethyltin chloride (3.16 g, 15.8 mmol). Allow the reaction mixture to reach room temperature. Add brine (aprox. 50 mL) and extract with ethyl acetate (2×50 mL). Dry the combined organic layers over magnesium sulfate and concentrate under vacuum yielding 4.9 g of the title compound as colorless oil: 1H NMR (CDCl3, 300 MHZ) δ: 7.49 (d, J=4.8 Hz, 1H), 7.13 (d, J=4.4 Hz, 1H), 1.49 (s, 9H), 0.36 (s, 9H).

Workup

  1. customto reach room temperature
  2. extractionAdd brine (aprox. 50 mL) and extract with ethyl acetate (2×50 mL)
  3. dry with materialDry the combined organic layers over magnesium sulfate
  4. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-bb0a8ca5ba3449e3ba25bd1b0e7accba
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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