Water → HCID 178421609, compound

HRID 342393Notes

Reaction equation

HRID 342393 reaction equation
Cl[P: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.[OH2:35].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:35]=[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

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 110602032,4,8,10-Tetra-tert-butyl-6-chloro-12-methyl-12H-dibenzo[d,g][1,3,2]dioxaphosphocine

Product 1

HCID 178421609HCID 178421609, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5.5 g (11 mmol) of the compound of Example 7 in 100 mL of toluene at ambient temperature is added dropwise a solution of 0.20 mL (11 mmol) of distilled water in 3.0 mL (22 mmol) of triethylamine. After the addition is complete, the reaction mixture is stirred at room temperature for 15 minutes. The toluene is removed under vacuum and the residue is recrystallized twice from 50 mL of diethyl ether. The ether is removed in vacuo and the residue is dried under vacuum to give 3.95 g (74% yield) of the title compound as an off-white solid melting at 209° C.

Workup

  1. additionAfter the addition
  2. customThe toluene is removed under vacuum
  3. customthe residue is recrystallized twice from 50 mL of diethyl ether
  4. customThe ether is removed in vacuo
  5. customthe residue is dried under vacuum

Sources & evidence

ORD record
ord-b67ca26fd04a46eea5545e0f1741df61
Source dataset
uspto-grants-1999_01
Patent number
US05858905

Reaction notes

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