Potassium Carbonate → Ethyl 4-[4-(ethylmethanesulfonylamino)-2,2-dimethylchroman-6-yloxy]valerate

HRID 567061Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[CH2:11][CH:10]([N:12]([CH2:17][CH3:18])[S:13]([CH3:16])(=[O:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:19])[CH:8]=2)[O:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CC(N(C)C)=O>[CH2:17]([N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:19][CH:29]([CH3:28])[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:8]=2)[O:3][C:2]([CH3:1])([CH3:20])[CH2:11]1)[CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

1.5 g (5 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethylmethane-sulfonamide (Example 1g) were stirred at 80° C. for 30 min with 0.7 g of powdered potassium carbonate in 75 ml of DMA. 0.8 ml (5 mmol) of ethyl 5-bromovalerate was then added and the mixture was stirred at 120° C. for 120 min. After reaction was complete (TLC), the mixture was concentrated in vac., treated with ice water and aqueous hydrochloric acid and a crystalline crude product was obtained, which was chromatographed on silica gel using n-heptane/EA (2:1). Appropriate fractions were crystallized using petroleum ether, 1.5 g, m.p. 65-67° C.

Workup

customAfter reaction
concentrationthe mixture was concentrated in vac
addition, treated with ice water and aqueous hydrochloric acid

Sources & evidence

ORD record: ord-7e7168dcd8ca4ddcb112a8e878022307
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177449B1

Reaction notes

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