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Water → HCID 18397082, compound

HRID 850826
Notes
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Reaction equation

HRID 850826 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@@H:47]3[C@H:38]([C@H:39]4[C@@:43]([CH2:45][CH2:46]3)([CH3:44])[C:42](=O)[CH2:41][CH2:40]4)[CH:37]=[CH:36][C:35]=2[CH:34]=1.O>O1CCCC1>[F:1][C:2]([F:3])=[C:42]1[CH2:41][CH2:40][C@H:39]2[C@H:38]3[C@H:47]([CH2:46][CH2:45][C@:43]12[CH3:44])[C:48]1[CH:35]=[CH:34][C:33]([O:32][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][O:26]2)=[CH:50][C:49]=1[CH:36]=[CH:37]3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 2724682Lithium diisopropylamideHCID 15307268HCID 15307268, compoundHCID 15635908Difluoromethyldiphenylphosphine oxide

Product 1

HCID 18397082HCID 18397082, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A solution of 715 mg of difluoromethyldiphenylphosphine oxide in 36 ml of tetrahydrofuran is slowly mixed with 1.42 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 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraen-17-one in 10 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 added to water, extracted with ethyl acetate, washed with water as well as with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. 1.1 g of 17-difluoromethylene-3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraene is obtained as colorless crystals.

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. extractionextracted with ethyl acetate
  5. washwashed with water as well as with saturated sodium chloride solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-d0e4ecea23af4d0caf29b436a3d4a396
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