Boron trifluoride etherate → HCID 86713725, compound

HRID 1406060Notes

Reaction equation

HRID 1406060 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]([OH:33])[CH2:21][C:22]#[C:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[O:31][CH3:32])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Si](OC[C@@H]1CO1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.ClC1C=CC(C#C)=C(OC)C=1.C([Li])CCC.B(F)(F)F.CCOCC>>[C:14]([Si:1]([O:18][CH2:19][C@@H:20]1[CH2:21][CH2:22][C@H:23]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[O:31][CH3:32])[O:33]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 5

HCID 8000Boron trifluoride etherateHCID 11077853HCID 11077853, compoundHCID 86713726HCID 86713726, compoundHCID 867137271587729-01-8HCID 178418339Butyllithium

Product 1

HCID 86713725HCID 86713725, compound

Procedure

tert-Butyl{[(2S,5R)-5-(4-chloro-2-methoxyphenyl)tetrahydrofuran-2-yl]methoxy}diphenylsilane was prepared from (2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-5-(4-chloro-2-methoxyphenyl)pent-4-yn-2-ol using the general method of T. X. M. Nguyen et al., Letters in Organic Chemistry 2009, 6, 630-636. This alkyne was prepared via reaction of tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane with 4-chloro-1-ethynyl-2-methoxybenzene, using n-butyllithium and boron trifluoride diethyl etherate.

Sources & evidence

ORD record
ord-d0d57996d4e9460d84b6e3242ecf6a22
Source dataset
uspto-grants-2014_12
Patent number
US08916564B2

Reaction notes

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