Diisopropylamine → HCID 86738321, compound

HRID 2059301Notes

Reaction equation

HRID 2059301 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[Cl-].[Cl:22][CH2:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:43]=[C:44]1[CH2:61][CH2:60][C@@:59]2([CH2:62][CH:63]=O)[C@@H:46]([CH2:47][CH2:48][C@@H:49]3[C@@H:58]2[CH2:57][CH2:56][C@@:54]2([CH3:55])[C@H:50]3[CH2:51][CH2:52][C:53]2=[O:65])[CH2:45]1>O1CCCC1.O>[Cl:22][CH:23]=[CH:63][CH2:62][C@@:59]12[C@@H:58]3[C@H:49]([C@H:50]4[C@@:54]([CH2:56][CH2:57]3)([CH3:55])[C:53](=[O:65])[CH2:52][CH2:51]4)[CH2:48][CH2:47][C@H:46]1[CH2:45][C:44](=[O:43])[CH2:61][CH2:60]2

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 2724682Lithium diisopropylamideHCID 86738322HCID 86738322, compoundHCID 178418339Butyllithium

Product 1

HCID 86738321HCID 86738321, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of lithium diisopropylamide, prepared from 0.26 ml of diisopropylamine and 0.85 ml of a 2.1 M solution of butyllithium and 5 ml of tetrahydrofuran is added to a solution of 640 mg of (chloromethyl)triphenylphosphonium chloride in 5 ml of tetrahydrofuran at -70° C. After 10 minutes at -70° C., a solution of 560 mg of 3,17-dioxo-5α-androstane-19-carboxaldehyde in 4 ml of tetrahydrofuran is added and the mixture is allowed to warm to room temperature. The mixture is then poured into water and extracted with ether. The solvent is evaporated and the residue is purified by flash chromatography on silica gel in 50% ethyl acetate-hexane to give 10-(3-chloroprop-2-enyl)-5α-estrane-3,17-dione as a mixture of isomers.

Workup

  1. extractionextracted with ether
  2. customThe solvent is evaporated
  3. customthe residue is purified by flash chromatography on silica gel in 50% ethyl acetate-hexane

Sources & evidence

ORD record
ord-e023b0d560fb4d3b8d51546aaf7d14d4
Source dataset
uspto-grants-1982_03
Patent number
US04322416

Reaction notes

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