Diethyl Ether → 5'-Formyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

HRID 376208Notes

Reaction equation

HRID 376208 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[O:13][C:14]3([C:24]([CH3:26])([CH3:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]3[CH3:27])[CH:15]=[N:16][C:11]=2[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)C>ClCCl>[CH:2]([C:3]1[C:12]2[O:13][C:14]3([C:24]([CH3:25])([CH3:26])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]3[CH3:27])[CH:15]=[N:16][C:11]=2[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[O:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 193609175'-hydroxymethyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Product 1

HCID 153056895'-Formyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.36 g (1 mmol) of 5'-hydroxymethyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine] in 30 ml of dichloromethane is added to 0.42 g (1 mmol) of Dess-Martin reactant prepared according to the method published in J. Org. Chem., 1983, 48, 4155, in solution in 60 ml of anhydrous dichloromethane. The mixture is then stirred for 1 hour at ambient temperature. 100 ml of ethyl ether are then added. The solution is then filtered and then evaporated. The product is purified by chromatography on a column of silica (CH2Cl2 eluent).

Workup

  1. customprepared
  2. filtrationThe solution is then filtered
  3. customevaporated
  4. customThe product is purified by chromatography on a column of silica (CH2Cl2 eluent)

Sources & evidence

ORD record
ord-cdfd4a6911ed4bd5a6bd7f47f5fa6235
Source dataset
uspto-grants-2000_02
Patent number
US06019914

Reaction notes

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