Ethyl orthoformate → HCID 86741692, compound

HRID 1788675Notes

Reaction equation

HRID 1788675 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][CH2:16]3.[CH2:29]([O:31][CH:32](OCC)[O:33][CH2:34][CH3:35])[CH3:30]>B(F)(F)F.CCOCC>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:29]([O:31][CH:32]([O:33][CH2:34][CH3:35])[C@@H:21]1[CH2:22][C@@:23]2([CH3:24])[C@@H:18]([CH2:17][CH2:16][C@@H:15]3[C@@H:25]2[CH2:26][CH2:27][C@@:10]2([CH3:11])[C@H:12]3[CH2:13][CH2:14][C@@H:9]2[OH:8])[CH2:19][C:20]1=[O:28])[CH3:30]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 86741694HCID 86741694, compound

Product 1

HCID 86741692HCID 86741692, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Procedure

By the method of part A of Example 20 (5α,17β)-17-hydroxyandrostan-3-one trifluoroacetate (ester) (0.344 mole) was diethoxymethylated using triethylorthoformate (126 ml.) and boron trifluoride etherate (140 ml.). The product was crystallized from methanol, affording (2α,5α,17β)-2-(diethoxymethyl)-17-hydroxyandrostan-3-one trifluoroacetate (ester) (118.7 g., 71% yield, m.r. 122°-123° C.).

Workup

  1. customThe product was crystallized from methanol

Sources & evidence

ORD record
ord-e63f7957dff241c5a1dd872f8df4f4b8
Source dataset
uspto-grants-1987_08
Patent number
US04684636

Reaction notes

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