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Lithium diisopropylamide → HCID 15307275, compound

HRID 850835
Notes
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Reaction equation

HRID 850835 reaction equation
[F:1][CH:2](P(=O)(C1C=CC=CC=1)C1C=CC=CC=1)[F:3].C([N-]C(C)C)(C)C.[Li+].[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32][C:33]1[CH:50]=[CH:49][C:48]2[C:47]3[CH2:46][CH2:45][C@@:43]4([CH3:44])[C@@H:39]([CH2:40][CH2:41][C:42]4=O)[C:38]=3[CH2:37][CH2:36][C:35]=2[CH:34]=1>O1CCCC1.C(OCC)(=O)C.O>[F:1][C:2]([F:3])=[C:42]1[CH2:41][CH2:40][C@H:39]2[C:38]3[CH2:37][CH2:36][C:49]4[CH:50]=[C:33]([O:32][CH:27]5[CH2:28][CH2:29][CH2:30][CH2:31][O:26]5)[CH:34]=[CH:35][C:48]=4[C:47]=3[CH2:46][CH2:45][C@:43]12[CH3:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 15307274HCID 15307274, compoundHCID 15635908(Difluoromethyl)(oxo)diphenyl-lambda~5~-phosphane

Product 1

HCID 15307275HCID 15307275, compoundYield 60.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.7 g of difluoromethyldiphenylphosphine oxide in 85 ml of tetrahydrofuran is slowly mixed with 5.3 ml of 2 M lithium diisopropylamide solution at a bath temperature of -50° C., and it is stirred for 1 hour. Then, a solution of 1.5 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),8-tetraen-17-one in 42 ml of tetrahydrofuran is slowly added, stirred for 15 minutes, slowly heated at a bath temperature of from -50° C. to 100° C. and refluxed for 2.5 hours. For working-up, it is diluted with ethyl acetate and water, washed with water, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 1.0 g of 17-difluoromethylene-3-tetrahydropyranyloxy-estra-1,3,5(10),8-tetraene is obtained as colorless crystals with a melting point of 124-125° C., [α]D22 =+2.0° (c=0.525% in pyridine).

Workup

  1. stirringstirred for 15 minutes
  2. temperatureslowly heated at a bath temperature of from -50° C. to 100° C.
  3. temperaturerefluxed for 2.5 hours
  4. washwashed with water
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-a8a7f2a0ab67467f9e3074db75e5b883
Source dataset
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06018062

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes