Triphenylphosphine → 3-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazole

HRID 1821139Notes

Reaction equation

HRID 1821139 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:32][C:33]1([CH3:44])[O:38][CH2:37][C:36]([CH2:42][OH:43])([N+:39]([O-:41])=[O:40])[CH2:35][O:34]1.[CH3:45][C:46]1[CH:51]=[C:50]([C:52]2[N:56]=[C:55]([C:57]3[S:64][C:63]([CH3:65])=[C:62]4[C:58]=3[CH2:59][C@H:60]3[C:66]([CH3:68])([CH3:67])[C@H:61]34)[O:54][N:53]=2)[CH:49]=[C:48]([CH3:69])[C:47]=1O>C1COCC1>[CH3:32][C:33]1([CH3:44])[O:34][CH2:35][C:36]([CH2:42][O:43][C:47]2[C:48]([CH3:69])=[CH:49][C:50]([C:52]3[N:56]=[C:55]([C:57]4[S:64][C:63]([CH3:65])=[C:62]5[C:58]=4[CH2:59][C@H:60]4[C:66]([CH3:67])([CH3:68])[C@H:61]45)[O:54][N:53]=3)=[CH:51][C:46]=2[CH3:45])([N+:39]([O-:41])=[O:40])[CH2:37][O:38]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 300859(2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanolHCID 5462977Diethyl azodicarboxylateHCID 1354079142,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenol

Product 1

HCID 689833493-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazoleYield 40.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (161 mg, 0.615 mmol) in dry THF (2.5 mL) is added DEAD (0.097 mL, 0.615 mmol). The solution is stirred at rt for 1 h before (2,2-dimethyl-5-nitro-[1,3]dioxan-5-yl)-methanol (118 mg, 0.615 mmol) and 2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenol (150 mg, 0.410 mmol) is added. Stirring is continued for 7 days. The formed precipitate is collected, washed with isopropanol and dried under high vacuum to give 3-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazole (90 mg) as an almost colourless solid; LC-MS: tR=1.30 min, [M+1]+=540.28; 1H NMR (CDCl3): δ 7.77 (s, 2H), 4.50 (d, J=12.9 Hz, 2H), 4.29-4.21 (m, 4H), 3.10 (dd, J=6.4, 18.8 Hz, 1H), 2.93 (d, J=18.8 Hz, 1H), 2.43 (s, 3H), 2.28 (s, 6H), 2.00-1.91 (m, 2H), 1.48 (s, 3H), 1.45 (s, 3H), 1.15 (s, 3H), 0.76 (s, 3H).

Workup

  1. additionis added
  2. customThe formed precipitate is collected
  3. washwashed with isopropanol
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-0e077bd9a1644d41805324e6b6fc03ac
Source dataset
uspto-grants-2009_10
Patent number
US07605269B2

Reaction notes

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