Disiloxane → HCID 12992812, compound

HRID 1760269Notes

Reaction equation

HRID 1760269 reaction equation
[SiH3]O[SiH3].[CH:4]1([O:7][C:8]2[CH:9]=[C:10]([CH2:18][O:19][Si](C(C)C)(C(C)C)C(C)C)[CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH2:6][CH2:5]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:4]1([O:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:16])[F:17])[CH2:18][OH:19])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 123318DisiloxaneHCID 2724141Tetrabutylammonium FluorideHCID 22598017HCID 22598017, compound

Product 1

HCID 12992812HCID 12992812, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the silyl ether, 3-Cyclopropyloxy-4-difluoromethoxy-1-(triisopropylsilyloxy)methylbenzene, from Step 4 (70 g, 179 mmol) in TBF (700 mL) at room temperature was added TBAF (215 mL of a 1M solution in THF, 215 mmol) and the resulting mixture was stirred for 17 h. The mixture was partitioned between 25% aq. NH4OAc (500 mL) and ethyl acetate (1 L) and the aqueous layer was extracted with ethyl acetate (2×). The combined organics were washed with brine, dried (Na2SO4) and concentrated. Flash chromatography of the residue (silica gel; hexane/ethyl acetate 3:2 to 1:1) provided the 3-Cyclopropyloxy-4-difluoromethoxybenzyl alcohol compound (41 g).

Workup

  1. customThe mixture was partitioned between 25% aq. NH4OAc (500 mL) and ethyl acetate (1 L)
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4b42c5e2076441e780a7648ca08e9d3b
Source dataset
uspto-grants-2005_01
Patent number
US06841564B2

Reaction notes

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