Tetrahydrofuran → HCID 59259718, compound

HRID 642957Notes

Reaction equation

[H-].[Na+].O1CCCC1.[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[CH2:18]([Sn:22]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23]I)[CH2:19][CH2:20][CH3:21]>C(OCC)(=O)C>[CH2:18]([Sn:22]([CH2:23][O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of sodium hydride (60%, 278 mg, 6.96 mmol) and tetrahydrofuran (20 ml) was added N-(3-hydroxypropyl)morpholine (963 μl, 6.96 mmol) at room temperature. Then, the reaction mixture was stirred at 45° C. (external temperature) for 10 minutes. To the reaction mixture was added tributyl-iodomethyl-tin (2.0 g, 4.64 mmol) at 0° C. (external temperature). Then, the mixture was stirred at 45° C. for 1 hour. The reaction mixture was cooled at room temperature, diluted with ethyl acetate, washed sequentially with water and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, heptane:ethyl acetate=9:1) to obtain the title compound (2.08 g, 6.96 mmol, 100%).

Workup

stirringThen, the mixture was stirred at 45° C. for 1 hour
temperatureThe reaction mixture was cooled at room temperature
washwashed sequentially with water
dry with materialan aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (NH silica gel, heptane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-fdd253d4e90c49f38c3674193535ab65
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696347B2

Reaction notes

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