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tert-Butyl methyl ether → (+/-)-cis-4-Trityloxy-2-cyclopentenol

HRID 2393907
Notes
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Reaction equation

HRID 2393907 reaction equation
[C:1]([O:20][CH:21]1[CH2:25][C:24](=[O:26])[CH:23]=[CH:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[I-].[Li+].COC(C)(C)C>C1(C)C=CC=CC=1>[C:1]([O:20][C@@H:21]1[CH2:25][C@H:24]([OH:26])[CH:23]=[CH:22]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 66321Lithium iodideHCID 109914404-Trityloxy-2-cyclopentenoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 10980801(+/-)-cis-4-Trityloxy-2-cyclopentenolYield 95%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
-20 °C

Procedure

A slurry of 4-trityloxy-2-cyclopentenone (1.03 g, 3.03 mmol, prepared in example 27) in toluene (8 mL) is cooled to -20° C. and treated sequentially with lithium aluminum hydride (76 mg, 2.0 mL), lithium iodide (1.06 g, 7.9 mmol) and dropwise with tert-butyl methyl ether (2 mL, over 5 minutes). The reaction is stirred for 1 hour at -20° C., warmed to 0° C. over 30 minutes, and stirred at 0° C. to 15° C. for 4 hours. The reaction is quenched by slow addition of 1N NaOH (2 mL) and then the reaction is filtered. The solids are washed with tert-butyl methyl ether and the phases of the filtrate are separated. The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by column chromatography (silica gel, 20% ethyl acetate/hexane) to provide the title compound as a white foam (980 mg, 95%). 1H NMR (CDCl3) δ 7.5 (m, 6 H), 7.3 (m, 9 H), 5.79 (d, 1 H), 5.14 (d, 1 H), 4.5 (m, 1 H), 4.4 (m, 1 H), 2.2 (m, 1 H), 1.42 (d, 1 H); 13C NMR (CDCl3) δ 145.1, 136.2, 135.9, 129.0, 128.1, 127.3, 87.7, 77.4, 74.9, 43.2; IR (KBr) νmax 3422, 3057, 1491, 1364, 1084, 1065, 1024 cm-1. Example 28a

Workup

  1. temperaturewarmed to 0° C. over 30 minutes
  2. stirringstirred at 0° C. to 15° C. for 4 hours
  3. customThe reaction is quenched by slow addition of 1N NaOH (2 mL)
  4. filtrationthe reaction is filtered
  5. washThe solids are washed with tert-butyl methyl ether
  6. customthe phases of the filtrate are separated
  7. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue is purified by column chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-59602782c691486ba36a1986b47f7159
Source dataset
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05808112

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes