Acetaldehyde → HCID 11215385, compound

HRID 1829629Notes

Reaction equation

HRID 1829629 reaction equation
Br[C:2](Br)=[CH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@H:13]([CH2:14][C@H:15]([O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:17]1)[CH2:12][CH2:11]3.[Li]CCCC.[CH:47](=[O:49])[CH3:48].Cl>C1COCC1>[Si:24]([O:23][C@@H:15]1[CH2:16][CH2:17][C@@:18]2([CH3:19])[C@@H:13]([CH2:12][CH2:11][C@@H:10]3[C@@H:20]2[CH2:21][CH2:22][C@@:5]2([CH3:6])[C@H:7]3[CH2:8][CH2:9][C@@H:4]2[C:3]#[C:2][CH:47]([OH:49])[CH3:48])[CH2:14]1)([C:37]([CH3:38])([CH3:40])[CH3:39])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 11331470HCID 11331470, compoundHCID 178418339Butyllithium

Product 1

HCID 11215385HCID 11215385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dibromo-2-[3α-(t-butyidiphenylsilyloxy)-5α-androstan-17β-yl]-ethylene (308 mg, 0.44 mmol) in THF (11 mL) was added at −78° C. a solution of n-BuLi 1.6 M in hexanes (2.76 mL, 4.4 mmol) and the mixture was stirred for 2 h. Acetaldehyde (0.032 mL, 0.57 mmol) was added at −78° C. and the temperature was let to rise to 25° C. Addition of HCl solution 2N at 0° C. was followed by extraction with ethyl acetate. The organic layer was washed with NaHCO3 brine and dried with (Na2SO4) and the solvent was evaporated in vacuo. Subsequent purification of the residue with flash column chromatography using petroleum etherlethyl acetate 90/10 as eluent afforded the desired compound named above.

Workup

  1. customto rise to 25° C
  2. extractionwas followed by extraction with ethyl acetate
  3. washThe organic layer was washed with NaHCO3 brine
  4. dry with materialdried with (Na2SO4)
  5. customthe solvent was evaporated in vacuo
  6. customSubsequent purification of the residue with flash column chromatography

Sources & evidence

ORD record
ord-19b0f118eb3c48118b61c16033b75aca
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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