Water → HCID 68283038, compound

HRID 1527191Notes

Reaction equation

HRID 1527191 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH:21]=[O:22])=[CH:13]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.O.[O-:29]Cl=O.[Na+]>C1COCC1.C(O)(C)(C)C>[CH2:1]([O:8][CH2:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]([OH:29])=[O:22])=[CH:13]1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86673811HCID 86673811, compound

Product 1

HCID 68283038HCID 68283038, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(2-benzyloxy-acetyl)-1H-indole-3-carbaldehyde (1.53 g, 5.22 mmol) in a mixture of THF (80 mL) and t-butanol (24 mL). A 2 M 2-methyl-2-butene solution in THF (104 mL, 209 mmol) was added, followed by a water (20 mL) solution of NaClO2 (80%, 5.9 g, 52.2 mmol) and NaH2PO4 (5 g, 41.7 mmol). The resulting yellow solution was stirred at RT for 2 h. The solvents were concentrated and the aqueous layer was filtered and the resulting precipitate was washed with Et2O to give the desired compound. LC/MS: 310.1 [M−H]−, 332.0 [M+Na]+, 308.0 [M−H]−, 617.0 [2M−H]−; tR (HPLC conditions a): 3.62 min.

Workup

  1. concentrationThe solvents were concentrated
  2. filtrationthe aqueous layer was filtered
  3. washthe resulting precipitate was washed with Et2O

Sources & evidence

ORD record
ord-82638d707a2046c1984ea744ad592d81
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…