18-Crown-6 → HCID 57256948, compound

HRID 1385624Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:9]([CH2:10][CH2:11][C:12]3[C:13]4[C@:20]([CH3:28])([CH2:21][CH2:22][C:23]=32)[C@@H:16]([C@@H:17]([OH:19])[CH3:18])[CH2:15][CH:14]=4)[C:8]1([CH3:30])[CH3:29])[CH3:5])[CH3:2].CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:56][CH:57]=[C:58]([CH3:60])[CH3:59]>O.C1(C)C=CC=CC=1>[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:9]([CH2:10][CH2:11][C:12]3[C:13]4[C@:20]([CH3:28])([CH2:21][CH2:22][C:23]=32)[C@@H:16]([C@H:17]([CH3:18])[O:19][CH2:56][CH:57]=[C:58]([CH3:60])[CH3:59])[CH2:15][CH:14]=4)[C:8]1([CH3:30])[CH3:29])[CH3:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

xvii)—A mixture of (3β,5α,20S)-3-[(1-ethoxyethyl)oxy]-4,4-dimethylpregna-8,14-dien-20-ol (17; 1.65 g), dry toluene (115 ml), potassium t-butoxide (5.68 g), 18-crown-6 (0.99 g) and 4-bromo-2-methyl-2-butene (4.44 ml) was heated at 70° C. for 1 h. After cooling, the reaction mixture was poured into water and the product extracted into ethyl acetate. The combined organic phases were washed with water and with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,5α,20S)-3-[(1-ethoxyethyl)oxy]-4,4-dimethyl-22-oxacholesta-8,14,24-triene (compound 18; 2.30 g), which was used in the following step without further purification.

Workup

temperatureAfter cooling
extractionthe product extracted into ethyl acetate
washThe combined organic phases were washed with water and with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6f1b7db57a6d4368b82e4fa6d62264e1
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262282B1

Reaction notes

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