Sodium Hydroxide → HCID 69625181, compound

HRID 1837031Notes

Reaction equation

[BH4-].[Na+].[OH-].[Na+].[CH2:5]([C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([O:25][CH3:26])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:27])[CH2:11][CH:10]=1)[CH3:6]>CO.ClCCl>[CH2:5]([C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([O:25][CH3:26])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C@@H:12]([OH:27])[CH2:11][CH:10]=1)[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

ix)—A solution of sodium borohydride (0.21 g) and sodium hydroxide (0.44 g) in methanol (50 ml) was added dropwise to a solution of (7α)-7-ethyl-3-methoxyestra-1,3,5(10),14-tetraen-17-one (4.31 g) in dichloromethane (12 ml) and methanol (20 ml), cooled to 0° C. The reaction mixture was stirred for 1.5 h, quenched with acetone (4 ml), and then poured into a saturated aqueous solution of ammonium chloride. The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure, to give (7α,17β)-7-ethyl-3-methoxyestra-1,3,5(10),14-tetraen-17-ol (4.28 g). The product was used in the following step without further purification.

Workup

customquenched with acetone (4 ml)
additionpoured into a saturated aqueous solution of ammonium chloride
extractionThe product was 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-2e4e9df18902417c854d687561ecc0ac
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780854B2

Reaction notes

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