Triethylamine → HCID 21251844, compound

HRID 1532420Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[CH:14][C:15](=[O:17])[O:16][C:11]=2[CH:10]=1.C(N(CC)CC)C.C(C1[C:36]([OH:37])=[C:35]([C:38](C)(C)C)[CH:34]=C(C)C=1)(C)(C)C.C(Cl)(=O)C(C)=C>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:38][C:35](=[CH2:34])[C:36]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[CH:14][C:15](=[O:17])[O:16][C:11]=2[CH:10]=1)=[O:37]

Participants

Conditions

Temperature: 0 °C

Procedure

4.2 g (16 mmol) of 7-(6-hydroxy-hexyloxy)-2H-1 -benzopyran-2-one were dissolved in 40 ml of absolute tetrahydrofuran with the exclusion of moisture, treated with 1.82 g (18 mmol) of triethylamine, 0.004 g (0.3 mmol) of 4-dimethylaminopyridine and a spatula tip of 2,6-di-tert.-butyl-p-cresol and cooled to 0° C. 1.7 ml of methacryloyl chloride were added dropwise to this solution within 10 min. The mixture was stirred at 0° C. for one hour and at room temperature for a further hour. Subsequently, the white precipitate which separated was filtered off and rinsed with tetrahydrofuran. The filtrate was evaporated to dryness and the residue was chromatographed on silica gel with acetone/cyclohexane (1:4). In this manner there were obtained 4 g of 6-(2-oxo-2H-1-benzopyran-7-yloxy)-hexyl 2-methyl-acrylate as a colourless liquid. λmax. (in CH2Cl2)=322.7 nm (ε=15110 l/mol cm).

Workup

customSubsequently, the white precipitate which separated
filtrationwas filtered off
washrinsed with tetrahydrofuran
customThe filtrate was evaporated to dryness
customthe residue was chromatographed on silica gel with acetone/cyclohexane (1:4)

Sources & evidence

ORD record: ord-929dd2aa7188498caff30ae265199de4
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201087B1

Reaction notes

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