3-Chloro-2-methyl-1-propene → HCID 57002804, compound

HRID 1385628Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:9]([CH2:10][CH2:11][C:12]3[C:13]4[C@:21]([CH3:29])([CH2:22][CH2:23][C:24]=32)[C@@H:16]([C@H:17]([CH3:20])[CH2:18][OH:19])[CH2:15][CH:14]=4)[C:8]1([CH3:31])[CH3:30])[CH3:5])[CH3:2].[CH3:32][C:33]([CH3:36])([O-])[CH3:34].[K+].C1OCCOCCOCCOCCOCCOC1.ClCC(C)=C>O.C1(C)C=CC=CC=1>[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:9]([CH2:10][CH2:11][C:12]3[C:13]4[C@:21]([CH3:29])([CH2:22][CH2:23][C:24]=32)[C@@H:16]([C@H:17]([CH3:20])[CH2:18][O:19][CH2:34][C:33]([CH3:36])=[CH2:32])[CH2:15][CH:14]=4)[C:8]1([CH3:31])[CH3:30])[CH3:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

vii)—A mixture of (3β,5α,20S)-3-[(1-ethoxyethyl)oxy]-4,4,20-trimethylpregna-8,14-dien-21-ol (1.0 g), dry toluene (67 ml), potassium t-butoxide (3.34 g), 18-crown-6 (0.581 g) and 3-chloro-2-methyl-1-propene (1.14 ml) was heated at 70° C. for 1.5 h. After cooling, the reaction mixture was poured into water and the product extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,5α,20S)-3-[(1-ethoxyethyl)oxy]-4,4-dimethyl-23-oxacholesta-8,14,25-triene (1.21 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 brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-fe3f4cb04eb0496b8347ecbb634728c5
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262282B1

Reaction notes

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