Dicyclohexylcarbodiimide → HCID 22272244, compound

HRID 2373105Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C:2]#[C:3][CH3:4].[CH:7]1[C:19]2[CH:18]([CH2:20]O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([O:6][CH2:20][CH:18]1[C:19]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:5])[C:2]#[C:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

First, 9-fluorenylmethyl 2-butynoate was prepared. A mixture of 2-butynoic acid (11.6 g, 138 mmol), 9-fluorenemethanol (35.2 g, 179 mmol), dimethylamino-pyridine-p-toluenesulfonic acid salt (16.3 g, 55 mmol), and anhydrous dichloromethane (210 mL) was cooled to 0° C. under nitrogen, and 1,3-dicyclohexylcarbodiimide (34.2 g, 166 mmol) was added. After 15 min, the reaction mixture was warmed to ambient and stirred for 12 h. The urea by product was filtered, and the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine. The solution was dried (Na2SO4) and concentrated to deposit a yellow oil. The product was purified by column chromatography to provide 20.0 g (54% of theory) of 9-fluorenylmethyl 2-butynoate as a yellow-green solid. 1H NMR (CDCl3): δ 1.98 (s, 3H), 4.20 (m, 1H), 4.45 (d, 2H), 7.32 (m, 4H), 7.60 (d, 2H), 7.70 (d, 2H).

Workup

customFirst, 9-fluorenylmethyl 2-butynoate was prepared
temperaturethe reaction mixture was warmed to ambient and
filtrationThe urea by product was filtered
washthe filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
dry with materialThe solution was dried (Na2SO4)
concentrationconcentrated
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-95be2cac9a0747a79c16bc824ba6af92
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459263B2

Reaction notes

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