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3,4-dihydro-2H-pyran → HCID 178418655, compound

HRID 1707907
Notes
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Reaction equation

HRID 1707907 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.S(O[Si](C)(C)C)(O[Si](C)(C)C)(=O)=O>ClCCl>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 87573Silanol, trimethyl-, 1,1'-sulfateHCID 178418615HCID 178418615, compound

Product 1

HCID 178418655HCID 178418655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3.0 g of trans-4-(4'-cyano-4biphenylyl)cyclohexanol. 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether.

Workup

  1. washwashed once with sodium carbonate solution and twice with water
  2. dry with materialsubsequently dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1)
  6. customRecrystallization from ethyl acetate at -20° C.

Sources & evidence

ORD record
ord-299af08171174dbcac6750aa326f0f12
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05356563

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes