HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 1-[(3-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-[(3-Benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester | HCID 10503415 | — |
| Reactant | Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate | HCID 10729163 | — |
| Reactant | 3-(Benzyloxy)benzyl chloride | HCID 13173490 | — |
| Product | 1-[(3-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid | HCID 23368763 | 42% |
Reaction Steps
1-[(3-Benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester. Using the procedure described in Example 1 Part F, 494 mg (2 mmol) of 5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester was reacted with 80 mg (2 mmol) of 60% NaH/mineral oil and 465 mg (2 mmol) of meta-benzyloxybenzyl chloride and after chromatography on silica (eluting with 20% EtOAc/hexane) and crystallizing from MeOH there was obtained 376 mg (42%) of 1-[(3-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid, mp, 60°-70° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05578634 |
| Source dataset | uspto-grants-1996_11 |
| ORD ID | ord-e09ae1c4789049a08a135cf93bc02c55 |
| Source note | uspto-grants-1996_11 |