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Water → 6-[(4-tert-Butylphenyl)(fluoro)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

HRID 1516720
Notes
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Reaction equation

HRID 1516720 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[C:12]2[C:13]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[C:14]3[C:22](=[CH:23][C:24]=2[CH:25]([CH3:27])[CH3:26])[O:21][C:17]2([CH2:20][CH2:19][CH2:18]2)[CH2:16][C:15]3=[O:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:43])CC)C.O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([F:43])[C:12]2[C:13]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[C:14]3[C:22](=[CH:23][C:24]=2[CH:25]([CH3:26])[CH3:27])[O:21][C:17]2([CH2:18][CH2:19][CH2:20]2)[CH2:16][C:15]3=[O:28])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 580029576-[(4-tert-Butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

Product 1

HCID 580030226-[(4-tert-Butylphenyl)(fluoro)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
-78 °C

Procedure

Under argon, 110 mg (0.23 mmol) of 6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1′-cyclobutan]-4(3H)-one (Example 55A) are dissolved in 2.3 ml of toluene, 36 μl (0.27 mmol) of diethylaminosulfur trifluoride are added slowly at −78° C. and the mixture is stirred at −78° C. for 1 h. The temperature is then slowly increased to −60° C. After 2 h, water is added and the mixture is extracted twice with ethyl acetate. The combined organic phases are washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 12:1). This gives 92 mg (83% of theory) of the title compound.

Workup

  1. temperatureThe temperature is then slowly increased to −60° C
  2. waitAfter 2 h
  3. extractionthe mixture is extracted twice with ethyl acetate
  4. washThe combined organic phases are washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 12:1)

Sources & evidence

ORD record
ord-2407f9c0df3c4b1ba65fbbf53f06c7aa
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08227511B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes