Diazomethane → HCID 21553924, compound

HRID 267778Notes

Reaction equation

HRID 267778 reaction equation
[OH:1][C:2]1([CH2:14][NH:15][CH:16]([CH3:18])[CH3:17])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:5]=2[O:4][CH2:3]1.[N+](=[CH2:21])=[N-]>C(OCC)C>[OH:1][C:2]1([CH2:14][NH:15][CH:16]([CH3:18])[CH3:17])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([O:13][CH3:21])=[CH:12][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 15557332HCID 15557332, compound

Product 1

HCID 21553924HCID 21553924, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3,7-Dihydroxy-3-isopropylaminomethyl-3,4-dihydro-2H-1,5-benzodioxepin (2.53 g.; 10 millimoles) from Example 89 dissolved in 50 ml. of diethyl ether is left 10 hours at ambient temperature with 0.46 g. (11 millimoles) of diazomethane in 25 ml. of diethyl ether. Excess diazomethane is destroyed by addition of a few drops of acetic acid. The solution then is washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness to give 3-hydroxy-3-isopropylaminomethyl-7-methoxy-3,4-dihydro-2H-1,5-benzodioxepin.

Workup

  1. customExcess diazomethane is destroyed by addition of a few drops of acetic acid
  2. washThe solution then is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-dd022915aec14693bdc54228c89fd52c
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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