Bicyclo[3.1.0]hexan-2-ol → HCID 131710021, compound

HRID 1578460Notes

Reaction equation

HRID 1578460 reaction equation
[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCCCC.C([Li])CCC.[CH:32]12[CH2:37][CH:36]1[CH2:35][CH:34]([OH:38])[CH2:33]2.[CH:39]12C[CH:43]1[CH2:42][CH2:41][CH:40]2[OH:45]>CCCCCC.C1C=CC=CC=1>[O:45]1[CH2:39][CH2:43][CH2:42][CH2:41][CH:40]1[O:38][CH:34]1[CH2:35][CH:36]2[CH:32]([CH2:37]2)[CH2:33]1

Participants

7

Reactant 4

HCID 276343Bicyclo[3.1.0]hexan-2-olHCID 2724569Phosphonium, hexyltriphenyl-, bromide (1:1)HCID 12724622Bicyclo(3.1.0)hexan-3-olHCID 178418339Butyllithium

Product 1

HCID 131710021HCID 131710021, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of hexyltriphenylphosphonium bromide (102 g.) and benzene (1200 ml.) is stirred under nitrogen during addition of a solution of butyl lithium in hexane (146 ml. of a 15% solution- w/v). The resulting mixture is stirred 30 min. Then a solution of the mixture (27 g.) of products obtained according to Preparation 4 in 300 ml. of benzene is added dropwise with stirring during 30 min. The mixture is heated and stirred at 70°C. for 2.5 hrs., and then is cooled to 25°C. The resulting precipitate is collected by filtration and washed with benzene. The filtrate and benzene wash are combined, washed with water, and dried to give 58 g. of a mixture of the tetrahydropyranyl ethers of endo-6-(cis- and trans-1-heptenyl)bicyclo[3.1.0]hexan-3-ol and endo-6-(cis- and trans-1-heptenyl)bicyclo[3.1.0]hexan-2-ol.

Workup

  1. customThen a solution of the mixture (27 g.) of products obtained
  2. customaccording to Preparation 4 in 300 ml
  3. stirringwith stirring during 30 min
  4. temperatureThe mixture is heated
  5. stirringstirred at 70°C. for 2.5 hrs
  6. filtrationThe resulting precipitate is collected by filtration
  7. washwashed with benzene
  8. washThe filtrate and benzene wash
  9. washwashed with water
  10. customdried
  11. customto give 58 g

Sources & evidence

ORD record
ord-cc678afa12a344e780c88072025802a4
Source dataset
uspto-grants-1976_02
Patent number
US03936487

Reaction notes

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