Thionyl Chloride → HCID 67251530, compound

HRID 41594Notes

Reaction equation

HRID 41594 reaction equation
O[CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][N:7]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].S(Cl)([Cl:21])=O>ClCCl>[Cl:21][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][N:7]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67251112Tert-butyl 4-(hydroxymethyl)-2,3-dihydro-1h-indole-1-carboxylate

Product 1

HCID 67251530HCID 67251530, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(hydroxymethyl)indoline-1-carboxylate (230 mg, 0.92 mmol) in dichloromethane (3 mL), thionyl chloride (0.123 mL, 1.02 mmol) was added dropwise at 0° C. and stirred for 1 h. Then the mixture was allowed to warm to rt and stirred overnight. The reaction mixture was concentrated under reduced pressure and dried under high vacuum to yield the title compound (217 mg, crude). The compound was directly used for the next step. [TLC Rf=0.86 (ethyl acetate/hexane 20:80)].

Workup

  1. stirringstirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-30a7155deafa4fe2a6fa4d04f3abf0d7
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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