Boron trifluoride etherate → HCID 68724788, compound

HRID 1471399Notes

Reaction equation

HRID 1471399 reaction equation
[CH3:1][C:2]1[CH:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]2([CH2:9][CH2:10][CH:11]=1)[CH2:8][CH2:7][CH2:6][CH2:5]2.CC1CCCC2(CCCC2)C=1C(OC)=O.CC1C(C(OC)=O)C2(CCC=1)CCCC2.CC12OC1CCC1(CCCC1)C2C(OCC)=O.OC1CCC2(CCCC2)C(C(OCC)=O)=C1C.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[CH3:1][C:2]1[CH2:11][CH2:10][CH2:9][C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

9

Reactant 7

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 68724110HCID 68724110, compoundHCID 68725689HCID 68725689, compoundHCID 68725948HCID 68725948, compoundHCID 68726408HCID 68726408, compoundHCID 86647586HCID 86647586, compound

Product 1

HCID 68724788HCID 68724788, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from ethyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (prepared as described in Example 14), as described for the preparation of methyl 7-methylspiro[4.5]dec-6-ene-6-carboxylate from methyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (Example 26), via crude ethyl 1-methyl-7-oxaspiro[bicyclo[4.1.0]heptane-3,1′-cyclopentane]-2-carboxylate (MCPBA, CH2Cl2), transformed into crude ethyl 8-hydroxy-7-methylspiro[4.5]dec-6-ene-6-carboxylate (NaOEt, reflux, 4 h) that was reduced using triethylsilane and BF3.OEt2 in dichloromethane (64% overall yield after FC (400 g SiO2, hexane/MTBE 40:1)).

Sources & evidence

ORD record
ord-a99b6c4e8cc8437abf731d48127ebb8c
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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