Carbon Tetrachloride → 1-tert-Butyl-3-(chloromethyl)azetidine
Reaction equation
[C:1]([N:5]1[CH2:8][CH:7]([CH2:9]O)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:31]>>[C:1]([N:5]1[CH2:8][CH:7]([CH2:9][Cl:31])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
A mixture of 3.0 g. (0.209 mol.) of N-t-butyl-3-hydroxymethylazetidine, 6.0 g. (0.0229 mol.) of triphenylphosphine and 50 ml. of carbon tetrachloride was refluxed for 48 hours. The mixture was cooled, filtered and the filtrate was extracted three times with 10% aqueous sulfuric acid. The combined extracts were basicified by addition of solid sodium carbonate and the basic solution was extracted with ether. The extract was dried (MgSO4), evaporated to dryness and the residue distilled to give N-t-butyl-3-chloromethylazetidine, b.p. 90°-96° (27 mm.).
Workup
- additionA mixture of 3.0 g
- temperatureThe mixture was cooled
- filtrationfiltered
- extractionthe filtrate was extracted three times with 10% aqueous sulfuric acid
- additionThe combined extracts were basicified by addition of solid sodium carbonate
- extractionthe basic solution was extracted with ether
- dry with materialThe extract was dried (MgSO4)
- customevaporated to dryness
- distillationthe residue distilled
Sources & evidence
- ORD record
- ord-eda848196bee4af0a3efdf1626c45591
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03983245
Reaction notes
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