4-Hydroxybiphenyl → HCID 58822934, compound

HRID 459117Notes

Reaction equation

HRID 459117 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Si:32]([O:39][C@@H:40]1[CH2:44][CH2:43][C@@H:42]([OH:45])[CH2:41]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].[C:46]1([C:52]2[CH:57]=[CH:56][C:55](O)=[CH:54][CH:53]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1COCC1>[C:46]1([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH:51]=[CH:50][C:49]([O:45][C@H:42]2[CH2:43][CH2:44][C@@H:40]([O:39][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:41]2)=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 21062586HCID 21062586, compound

Product 1

HCID 58822934HCID 58822934, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphenylphosphine (0.195 g, 0.742 mmol) in 5 mL of dry THF was treated at 0° C. with diethylazodicarboxylate (0.117 mL, 0.742 mmol) and stirred for 20 min. A solution of (1R*,3R*)-3-(tert-butyldimethylsilanyloxy)cyclopentanol (0.146 g, 0.675 mmol) and 4-phenyl phenol (0.126 g, 0.0.724 mmol) in 5 mL of dry THF was added to the solution, and the mixture was stirred at room temperature overnight. The solution was concentrated under vacuum and purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 6:1, Rf0.66). 1H-NMR (200.15 MHz, CDCl3): δ 7.58–7.29 (m, 7H); 6.93 (d, 2H, J=8.92), 4.76–4.65 (m, 1H), 4.32–4.21 (m, 1H), 2.38 (qn, 1H, J=7.0), 2.04–1.94 (m, 2H), 1.87–1.78 (m, 3H), 0.90 (s, 9H), 0.07 (s, 3H), 0.06 (s, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe solution was concentrated under vacuum
  3. custompurified by silica gel chromatography (silica gel, hexanes/ethyl acetate 6:1, Rf0.66)

Sources & evidence

ORD record
ord-a6a7f66d2eef46cabc6b44821fe2747f
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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