tert-Butyl methyl ether → Didodecyl 2-(t-butylthio)-1-hydroxy-1-methylethanephosphonate

HRID 1079098Notes

Reaction equation

[P:1]([O-:28])([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].COC(C)(C)C.N12CCCNC1C=CCCC2.[C:46]([S:50][CH2:51][C:52](=[O:54])[CH3:53])([CH3:49])([CH3:48])[CH3:47]>C1(C)C=CC=CC=1.CS(C)=O>[C:46]([S:50][CH2:51][C:52]([OH:54])([CH3:53])[P:1]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:28])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH3:49])([CH3:48])[CH3:47]

Participants

Conditions

Temperature: 60 °C

Procedure

23.0 g (55 mmol) of didodecyl phosphite are initially introduced into a mixture of 20 ml of tert-butyl methyl ether and 5 ml of dimethyl sulfoxide. 1.0 g of 1,8-diazabicyclo[5.4.0]undec-5-ene (DBU) are added, and 8.04 g (55 mmol) of (t-butylthio)acetone are then added dropwise at 30° C. The reaction mixture is heated for 5 hours at 60° C., cooled, diluted with 150 ml of toluene and washed with 100 ml of water. The organic phase is dried over sodium sulfate, and the solvent and remainders of the educts are distilled off in vacuo (finally at 0.5 mbar and 55° C. bath temperature).

Workup

temperaturecooled
washwashed with 100 ml of water
dry with materialThe organic phase is dried over sodium sulfate
distillationthe solvent and remainders of the educts are distilled off in vacuo (finally at 0.5 mbar and 55° C. bath temperature)

Sources & evidence

ORD record: ord-b5843fedb2dc44da9fcd9d43da58a25d
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05550276

Reaction notes

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