Diethyl Ether → 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

HRID 1724028Notes

Reaction equation

C(N1C2C(=CC=CC=2)C([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=C1CO[Si](C(C)C)(C(C)C)C(C)C)C1C=CC=CC=1.[F-].C([N+:44]([CH2:53][CH2:54][CH2:55][CH3:56])([CH2:49][CH2:50][CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][CH3:48])CCC.[NH4+].[Cl-].C[CH2:60][O:61]CC.[CH2:64]1[CH2:68]OC[CH2:65]1>>[CH2:53]([N:44]1[C:45]2[C:51](=[CH:52][C:48]([C:17]([OH:26])([C:22]([F:23])([F:24])[F:25])[C:18]([F:20])([F:19])[F:21])=[CH:47][CH:46]=2)[CH:50]=[C:49]1[CH2:60][OH:61])[C:54]1[CH:55]=[CH:56][CH:68]=[CH:64][CH:65]=1

Participants

Reactant 5

HCID 3283Diethyl Ether

HCID 8028Tetrahydrofuran2×

HCID 25517Ammonium Chloride

HCID 2724141Tetrabutylammonium Fluoride

HCID 867608102-(1-benzyl-2-triisopropylsilanyloxymethyl-1H-indol--yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

Product 1

HCID 115604542-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

Procedure

To a solution of 0.93 g (1.66 mmol) of 2-(1-benzyl-2-triisopropylsilanyloxymethyl-1H-indol--yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 10 mL of THF were added 1.66 mL (1.66 mmol) of a 1 M solution of tetrabutyl ammonium fluoride in THF. The mixture was stirred at RT for 1 h and poured into a mixture of a saturated aqueous solution of NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 1.0 g (quantitative) of 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, light yellow semisolid, MS: 402 (M−H)−.

Workup

customThe phases were separated
extractionthe aqueous one was extracted with Et2O
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-5981af55b50b4093886a2e71a3d70f1a
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485652B2

Reaction notes

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