O,O-Dipyridin-2-yl carbonothioate → Tert-butyl[(8-isothiocyanato-1,2,3,4-tetrahydronaphthalen-2-yl)oxy]dimethylsilane

HRID 1785565Notes

Reaction equation

HRID 1785565 reaction equation
[Si:1]([O:8][CH:9]1[CH2:18][C:17]2[C:16]([NH2:19])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=C(O[C:27](OC2N=CC=CC=2)=[S:28])N=CC=1>ClCCl>[C:4]([Si:1]([O:8][CH:9]1[CH2:10][CH2:11][C:12]2[C:17](=[C:16]([N:19]=[C:27]=[S:28])[CH:15]=[CH:14][CH:13]=2)[CH2:18]1)([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 587341927-{[Tert-butyl(dimethyl)silyl]oxy}-5,6,7,8-tetrahydronaphthalen-1-amine

Product 1

HCID 75581950Tert-butyl[(8-isothiocyanato-1,2,3,4-tetrahydronaphthalen-2-yl)oxy]dimethylsilaneYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 18B, 2-(tert-butyldimethylsilyl)-ol (1.4 g, 5.07 mmol) and di-2-pyridyl thionocarbonate (1.07 g, 4.61 mmol) in 30 mL dichloromethane was stirred at room temperature overnight. The mixture was evaporated, then the residue was taken up in 2 mL dichloromethane and filtered through silica gel, eluting with 5% ethyl acetate-hexane. Evaporation of the filtrate afforded the product as a dark red oil (1.165 g, 72%). 1H NMR (DMSO-d6) δ 7.21 (m, 3H), 4.27 (m, 1H), 2.58-3.09 (m, 4H), 1.90 (m, 1H), 1.77 (m, 1H), 0.90 (s, 9H), 0.14 (s, 6H).

Workup

  1. customThe mixture was evaporated
  2. filtrationfiltered through silica gel
  3. washeluting with 5% ethyl acetate-hexane
  4. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-973473a85bce4c61ad758d2f94b5d00c
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

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