Diethyl Ether → HCID 86648912, compound

HRID 1886745Notes

Reaction equation

[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41].C(OCC)C>CN(C)C=O.C1CCCCC1>[C:1]([O:5][C:6](=[O:15])[CH:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 75 °C

Procedure

29.3 mmol (6.56 mL) of malonic acid di-tert-butyl ester and 29.3 mmol (1.28 g) of sodium hydride in mineral oil (55% (w/w)) were reacted in 120 mL of anhydrous dimethylformamide for 50 min at room temperature according to general procedure B2. 45.4 mmol (23.0 g) of 4′ were added to the mixture and the reaction mixture was stirred for 1 h at 75° C. bath temperature and at room temperature o/n. Additional 16.2 mmol (708 mg) of sodium hydride in mineral oil (55% (w/w)) were added and the reaction mixture was further stirred at room temperature for 7 h. The work-up was performed as described (general procedure B) with diethyl ether. Column chromatography (cyclohexane→cyclohexane/acetone 9:1) gave 5c′ with 67% yield.

Workup

customat room temperature
stirringthe reaction mixture was further stirred at room temperature for 7 h

Sources & evidence

ORD record: ord-ab29f206c0b84bf884cdd36779a2db99
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501199B2

Reaction notes

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