Tetrahydrofuran → HCID 69629895, compound

HRID 1792205Notes

Reaction equation

[Si:1]([O:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][CH2:26][C:27](N(C)C)=[O:28])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[Ce](Cl)Cl.[CH2:51]([Mg]Br)[CH3:52].O1CC[CH2:57][CH2:56]1>>[Si:1]([O:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][CH2:26][C:27]([CH2:51][CH3:52])([OH:28])[CH2:56][CH3:57])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 161282Cerium trichloride

HCID 69630482HCID 69630482, compound

HCID 178418443HCID 178418443, compound

Product 1

HCID 69629895HCID 69629895, compoundYield 51.7%

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(N,N-dimethylaminocarbonylethoxy)-20-methylpregna-5,7,16-triene (133 mg, 0.20 mmol), anhydrous cerous (III) chloride (2.17 g, 8.8 mmol), ethylmagnesium bromide (8.3 ml, 8.0 mmol) and tetrahydrofuran (10 ml) were subjected to reaction using a procedure similar to that of Example 25(2) (at 0° C. for 1 hour), worked up and purified by preparative thin layer chromatography (2 sheets (each 1.0 mm thickness), hexane:ethyl acetate=5:1) to give the titled compound (70.7 mg, 51.7%) as a colorless oil.

Workup

customof Example 25(2) (at 0° C. for 1 hour)
custompurified by preparative thin layer chromatography (2 sheets (each 1.0 mm thickness), hexane

Sources & evidence

ORD record: ord-f76a56a7c1944a91b3e37927785e3331
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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