Boron trifluoride etherate → (2alpha,5alpha,17beta)-2-(Diethoxymethyl)-17-methoxyandrostan-3-one

HRID 1788676Notes

Reaction equation

HRID 1788676 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3.[CH2:23]([O:25][CH:26](OCC)[O:27][CH2:28][CH3:29])[CH3:24].B(F)(F)F.CCOCC>>[CH2:23]([O:25][CH:26]([O:27][CH2:28][CH3:29])[C@@H:15]1[CH2:16][C@@:17]2([CH3:18])[C@@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:5])[C@H:6]3[CH2:7][CH2:8][C@@H:3]2[O:2][CH3:1])[CH2:13][C:14]1=[O:22])[CH3:24]

Participants

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 1104493517beta-Methoxy-5alpha-androstan-3-one

Product 1

HCID 54489025(2alpha,5alpha,17beta)-2-(Diethoxymethyl)-17-methoxyandrostan-3-oneYield 117.7%

Procedure

By the method of part A of Example 20 (5α,17β)-17-methoxyandrostan-3-one (45.67 g., 0.15 mole) was diethoxymethylated using triethylorthoformate (55.0 ml., 49.0 g., 0.33 mole) and boron trifluoride etherate (50.0 ml., 57.7 g., 0.407 mole), affording (2α,5α,17β)-2-(diethoxymethyl)-17-methoxyandrostan-3-one (71.81 g.).

Sources & evidence

ORD record
ord-2b1b0fd95f8c46db929f42c1c3e98c4e
Source dataset
uspto-grants-1987_08
Patent number
US04684636

Reaction notes

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