tert-Butyl methyl ether → HCID 178444519, compound

HRID 2050429Notes

Reaction equation

HRID 2050429 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH:17]=O)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.CO[C:21](C)(C)[CH3:22]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH2:15]([C@H:12]1[CH2:13][CH2:14][C@H:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([O:2][CH3:1])[CH2:4][CH2:5]2)[CH2:10][CH2:11]1)[CH2:16][CH:17]=[CH:21][CH3:22]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl ether2×HCID 178496561HCID 178496561, compound

Product 1

HCID 178444519HCID 178444519, compound

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Conditions

Temperature
0 °C

Procedure

2.65 g of ethyltriphenylphosphonium bromide were suspended in 40 ml of tert.butyl methyl ether while gassing with argon. The suspension was treated at room temperature with 797 mg of potassium tert.butylate and stirred for 1 hour. The mixture was subsequently cooled to 0° C., treated dropwise within 3 minutes with a solution of 1.1 g of 3-[trans-4-(trans-4-methoxycyclohexyl)cyclohexyl]propionaldehyde in 15 ml of tert.butyl methyl ether and then left to warm slowly to room temperature while stirring. After 2 hours the pale yellow suspension was partitioned between diethyl ether and water. The aqueous phase was separated and washed three times with diethyl ether. The organic phases were washed twice with water, dried over magnesium sulfate, filtered and evaporated. Chromatographic purification of the yellow, solid crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave 0.91 g of trans-4-(3-pentenyl)-1-(trans-4-methoxycyclohexyl)cyclohexane with a Z/E ratio of 86:11.

Workup

  1. waitleft
  2. temperatureto warm slowly to room temperature
  3. stirringwhile stirring
  4. customAfter 2 hours the pale yellow suspension was partitioned between diethyl ether and water
  5. customThe aqueous phase was separated
  6. washwashed three times with diethyl ether
  7. washThe organic phases were washed twice with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customChromatographic purification of the yellow, solid crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

Sources & evidence

ORD record
ord-963b01bbf5f244e3b1366b6283ee3c94
Source dataset
uspto-grants-1991_05
Patent number
US05013477

Reaction notes

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