Diisopropylamine → HCID 21959222, compound

HRID 2055045Notes

Reaction equation

C(NC(C)C)(C)C.[CH3:8][O:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:15]=[CH:14][C:13]=1[C:22]1[C:23](=[O:37])[O:24][C:25]2[C:30]([C:31]=1[CH3:32])=[CH:29][CH:28]=[C:27]([O:33][CH2:34][O:35][CH3:36])[CH:26]=2.[CH:38](OC1C=CC=CC=1)=[O:39]>C1COCC1>[CH3:8][O:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:15]=[CH:14][C:13]=1[C:22]1[C:23](=[O:37])[O:24][C:25]2[C:30]([C:31]=1[CH2:32][CH:38]=[O:39])=[CH:29][CH:28]=[C:27]([O:33][CH2:34][O:35][CH3:36])[CH:26]=2

Participants

Conditions

Temperature: -10 °C

Procedure

To a clean dry 200 ml flask purged with nitrogen was added diisopropylamine (2.7 ml, 19.5 mmol, 3 eq), dry THF (50 mL) and 3-(2,4-Bis-methoxymethoxy-phenyl)-7-methoxymethoxy-4-methyl-chromen-2-one (8.1 mL, 16.25 mmol, 2.5 eq.) at −78° C. After 30 minutes, to this solution was added drop-wise, a solution of 3-(2,4-bis-methoxymethoxy-phenyl)-7-methoxymethoxy-4-methyl-chromen-2-one (2.7 g, 6.5 mmol, 1 eq.) in dry THF (13 mL). The solution was warmed to −10° C. and stirred at this temperature for 30 minutes. Phenyl formate (3.6 ml, 33 mmol, 5 eq) was then added slowly into the reaction mixture. The reaction mixture was then stirred for 30 mins, quenched with saturated aqueous NH4Cl, extracted with ethyl acetate and then concentrated to yield th title product as a crude solid which was purified by flash chromatography eluting with 30% ethyl acetate in hexane to yield the title product as a solid.

Workup

customTo a clean dry 200 ml flask
custompurged with nitrogen
additionto this solution was added drop-wise
stirringThe reaction mixture was then stirred for 30 mins
customquenched with saturated aqueous NH4Cl
extractionextracted with ethyl acetate
concentrationconcentrated

Sources & evidence

ORD record: ord-e0fbb6dee1ef47c4acfcf4ec1fe8736b
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329654B2

Reaction notes

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