Tetrahydrofuran → HCID 68161628, compound

HRID 410012Notes

Reaction equation

HRID 410012 reaction equation
[Li]CCCC.[CH2:6]([C:12]1[O:13][C:14](I)=[CH:15][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Sn:18](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22].[O:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH2:27]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[C:36]1[O:32][C:33]([C:14]2[O:13][C:12]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:16][CH:15]=2)=[CH:34][CH:35]=1)[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 15096Tributyltin ChlorideHCID 67060813HCID 67060813, compoundHCID 178418339Butyllithium

Product 1

HCID 68161628HCID 68161628, compoundYield 20%

Conditions

Temperature
-78 °C

Procedure

A solution of n-BuLi (14.1 mL, 1.6 M in hexanes, 22.5 mmol, 1.3 equivalents) was added dropwise to a solution of 2-hexyl-5-iodofuran (3.8 g, 17.4 mmol) in dry tetrahydrofuran (THF, 100 mL) at −78° C. under N2. The reaction mixture was allowed to reach to room temperature and stirred for 1 h. The resulting mixture was cooled to −78° C., Bu3SnCl (6.1 mL, 22.5 mmol) was added dropwise and the reaction mixture was allowed to reach room temperature and stirred for 2 h. The mixture was quenched with water, extracted with hexane, dried (MgSO4), and evaporated. Flash chromatography on a basified (NEt3) silica, using hexane as eluent gave Tributyl(5′-hexyl-[2,2′-bifuran]-5-yl)stannane) (1.9 g, 20% yield) as a colorless oil. 1H NMR (300 MHz, CDCl3): ppm. 13C NMR (75 MHz, CDCl3): δ 106.1, 155.9, 151.4, 145.7, 122.9, 106.4, 105.4, 104.0, 31.6, 28.9, 28.8, 28.1, 28.0, 27.2 22.6, 14.7, 14.1, 10.2 ppm. FIRMS (FD): m/z calcd for C26H44O2Sn: 508.2368. found 508.2374.

Workup

  1. customto reach to room temperature
  2. customto reach room temperature
  3. stirringstirred for 2 h
  4. customThe mixture was quenched with water
  5. extractionextracted with hexane
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-4e64bb8880364f2aa0853cf953983568
Source dataset
uspto-grants-2014_06
Patent number
US08759550B2

Reaction notes

Loading…