2,3-Di(carboxymethyl)furan → HCID 19600257, compound
Reaction equation
[C:1]([CH2:4][C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH2:10][C:11](O)=[O:12])(O)=[O:2]>C1COCC1>[OH:2][CH2:1][CH2:4][C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH2:10][CH2:11][OH:12]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of the product from step c.) (6.4 g, 35 mmol) in dry THF (400 ml) was cooled to 0° C. and a 1.0 M solution of BH3 in THF (174 ml, 174 mmol) was added dropwise over 10 minutes. After the addition was complete the mixture was stirred for an additional 20 minutes at 0° C. and then warmed to 22° C. for 2 hours. Next, the mixture was poured into ice cold sat. NaHCO3 (300 ml) and extracted with EtOAc (2×200 ml). The organic layer was dried (MgSO4) and concentrated providing 3.58 g (65%) of the subtitle compound. MS: ESI (positive): 157 (M+H).
Workup
- additionAfter the addition
- temperaturewarmed to 22° C. for 2 hours
- extractionextracted with EtOAc (2×200 ml)
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9ad178c521d443ddbf2683bf7f2a8b1f
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718647B2
Reaction notes
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