Tetrahydrofuran → HCID 90332136, compound

HRID 2175402Notes

Reaction equation

[F-].C([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])CCCC)CCC.[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1>>[N:6]1[C:11]([C@H:21]2[CH2:20][C@@H:19]2[CH2:23][OH:22])=[CH:12][CH:13]=[C:14]2[CH2:18][CH2:17][CH2:16][C:15]=12

Participants

Reactant 2

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 90332136HCID 90332136, compound

Procedure

To a stirred solution of S-5 (3.19 g, 10.5 mmol) in THF (40 mL) was added tetrabutyl ammonium fluoride solution 1M (10.5 mL, 10.5 mmol). The resulting mixture was stirred 2 hours at room temperature and concentrated. Flash column separation using a 10-100% ethyl acetate/hexane gradient gave S-6 as an oil. (1.44 g, 72%)

Workup

concentrationconcentrated
customFlash column separation

Sources & evidence

ORD record: ord-8b68e44da54f4e2bb0b518bb68d13409
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062059B2

Reaction notes

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