Sodium hydride → 6-{[2,4,8,10-Tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin-6-yl]oxy}-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin

HRID 342394Notes

Reaction equation

HRID 342394 reaction equation
[O:1]=[PH:2]1[O:9][C:8]2[C:10]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:13][C:7]=2[CH:6]([CH3:22])[C:5]2[CH:23]=[C:24]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:4]=2[O:3]1.[H-].[Na+].Cl[P:38]1[O:45][C:44]2[C:46]([C:54]([CH3:57])([CH3:56])[CH3:55])=[CH:47][C:48]([C:50]([CH3:53])([CH3:52])[CH3:51])=[CH:49][C:43]=2[CH:42]([CH3:58])[C:41]2[CH:59]=[C:60]([C:67]([CH3:70])([CH3:69])[CH3:68])[CH:61]=[C:62]([C:63]([CH3:66])([CH3:65])[CH3:64])[C:40]=2[O:39]1>O1CCCC1>[C:14]([C:12]1[CH:11]=[C:10]([C:18]([CH3:19])([CH3:20])[CH3:21])[C:8]2[O:9][P:2]([O:1][P:38]3[O:45][C:44]4[C:46]([C:54]([CH3:55])([CH3:56])[CH3:57])=[CH:47][C:48]([C:50]([CH3:53])([CH3:51])[CH3:52])=[CH:49][C:43]=4[CH:42]([CH3:58])[C:41]4[CH:59]=[C:60]([C:67]([CH3:68])([CH3:70])[CH3:69])[CH:61]=[C:62]([C:63]([CH3:66])([CH3:65])[CH3:64])[C:40]=4[O:39]3)[O:3][C:4]3[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][C:24]([C:31]([CH3:33])([CH3:32])[CH3:34])=[CH:23][C:5]=3[CH:6]([CH3:22])[C:7]=2[CH:13]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 110602032,4,8,10-Tetra-tert-butyl-6-chloro-12-methyl-12H-dibenzo[d,g][1,3,2]dioxaphosphocineHCID 178421609HCID 178421609, compound

Product 1

HCID 883982766-{[2,4,8,10-Tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin-6-yl]oxy}-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 17.3 g (36 mmol) of the compound of Example 8 in 250 mL of dry tetrahydrofuran (THF) is added 1.0 g (41 mmol) of sodium hydride at 3° C. After the addition is complete, the reaction mixture is allowed to warm to room temperature. The reaction mixture is stirred for 14 hours at ambient temperature. To the reaction mixture is then added 14.8 g(29 mmol) of the compound of Example 7 at ambient temperature. After 48 hours, the reaction mixture is filtered and the filtrate is concentrated under vacuum. The residue is purified by flash chromatography with 1% ethyl acetate/99% hexane to give the tide compound as a white solid melting at 281°-285° C.

Workup

  1. additionAfter the addition
  2. waitAfter 48 hours
  3. filtrationthe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated under vacuum
  5. customThe residue is purified by flash chromatography with 1% ethyl acetate/99% hexane

Sources & evidence

ORD record
ord-e6e56a1e66384489b202f48ded3d5b6b
Source dataset
uspto-grants-1999_01
Patent number
US05858905

Reaction notes

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