tert-Butyl methyl ether → HCID 178444519, compound

HRID 1463750Notes

Reaction equation

HRID 1463750 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 in diethyl ether/water. The aqueous phase was separated and washed three times 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)-l-(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 in diethyl ether/water
  5. customThe aqueous phase was separated
  6. washwashed three times 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-f84510eef43b45d6801fbdd50875f31d
Source dataset
uspto-grants-1994_04
Patent number
US05302317

Reaction notes

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