1,1,3,3-Tetramethylguanidine → Triphenylphosphine Oxide

HRID 891252Notes

Reaction equation

[Cl-].C(OC([P+:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C(OCC)=O)C.C([O:37]C1C=CC(C=O)=CC=1)C1C=CC=CC=1.CN(C)C(=N)N(C)C>C(Cl)Cl>[CH:27]1[CH:28]=[CH:29][C:24]([P:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:37])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The crystals of (1,2-diethoxy-2-oxoethyl)(triphenyl)phosphonium chloride in the reactor were dissolved in CH2Cl2 (290 L) followed by the addition of 4-benzyloxybenzaldehyde (44.2 kg, 208 mol, yield is based on this chemical). To this solution tetramethylguanidine (25.4 kg, 220 mol) was added in 1 hour. The solution was then stirred for 20 hours at 20° C. CH2Cl2 (200 L) was distilled off and at an Ti of 30° C. replaced TBME (280 l). The crystals of TPPO formed were filtered off at 20° C. and the mother-liquor was concentrated until a new precipitate was formed. The TPPO was filtered off again and the mother-liquor was concentrated until no more solvents distilled. 2-Propanol (260 L) and seeding crystals (ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxy-2-propenoate) (50 g) were added before cooling to 0° C. The resulting suspension was filtered and the isolated material dried at 40° C./160 mbar. The overall yield was 44.5 kg, 65% (GLC: 99% area).

Workup

customyield
distillationCH2Cl2 (200 L) was distilled off and at an Ti of 30° C.

Sources & evidence

ORD record: ord-2b338be094624caa807baec91f251725
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07002037B2

Reaction notes

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