Tetrahydrofuran → HCID 14112562, compound

HRID 1576901Notes

Reaction equation

HRID 1576901 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH3:10])=[O:4].B#B.[O:13]1CCCC1>C(OCC)C>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH:8]([OH:13])[CH2:9][CH3:10])=[O:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5540505-Heptenoic acid, methyl esterHCID 6328200Diboron

Product 1

HCID 14112562HCID 14112562, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound XL is prepared by reacting endo-bicycle[3.1.0]hex-2-ene-6-carboxylic acid methyl ester with diborane in a mixture of tetrahydrofuran and diethyl ether, a reaction generally known in the art, to give endo-bicyclo[3.100]63 hexan-3-ol-6-carboxylic acid methyl ester which is then reacted with dihydropyran in the presence of a catalytic amount of POCl3 to give the desired compound. This is then used as described in said Belgian patent to produce the endo form of bicyclo-ketone XVI.

Workup

  1. customCompound XL is prepared
  2. customa reaction

Sources & evidence

ORD record
ord-989b507766c54a2cb7d908e5312409a3
Source dataset
uspto-grants-1976_09
Patent number
US03983154

Reaction notes

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