1H-Benzotriazole-1-methanol → HCID 86724237, compound

HRID 594845Notes

Reaction equation

HRID 594845 reaction equation
C[C:2](C)([O-:4])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:18](=[CH:19][CH:20]=1)[O:17][C:13]1([CH2:16][CH2:15][CH2:14]1)[CH2:12][C:11]2=[O:21].N1([CH2:31][OH:32])C2C=CC=CC=2N=N1>C1COCC1.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]2[C:18](=[CH:19][CH:20]=1)[O:17][C:13]1([CH2:14][CH2:15][CH2:16]1)[C:12]([CH2:2][OH:4])([CH2:31][OH:32])[C:11]2=[O:21]

Participants

6

Reactant 3

HCID 2241691H-Benzotriazole-1-methanolHCID 23665647Potassium tert-butoxideHCID 667462536-Bromospiro[1-benzopyran-2,1'-cyclobutan]-4(3H)-one

Product 1

HCID 86724237HCID 86724237, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of potassium tert-butoxide (441 mg, 3.93 mmol) in THF (5 mL) was added to a suspension of 6-bromospiro[chromene-2,1′-cyclobutan]-4(3H)-one (500 mg, 1.87 mmol) and 1H-benzotriazole-1-methanol (586 mg, 3.93 mmol) in THF (5 mL) over 10 minutes in a dry ice-acetone bath under an argon atmosphere. The mixture was stirred for 0.5 hours in an ice bath, and then diluted with EtOAc (10 mL). After stirring for 0.5 hours, the mixture was filtered off. The filtrate was washed with 0.2 M aqueous NaOH (two times), water and brine, dried over MgSO4 and silicagel, filtered off. The filtrate was evaporated to give crude 6-bromo-3,3-bis(hydroxymethyl)spiro[chromene-2,1′-cyclobutan]-4(3H)-one (641 mg).

Workup

  1. stirringAfter stirring for 0.5 hours
  2. filtrationthe mixture was filtered off
  3. washThe filtrate was washed with 0.2 M aqueous NaOH (two times), water and brine
  4. dry with materialdried over MgSO4 and silicagel
  5. filtrationfiltered off
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-8e4f8db5bb04459aa9692166d9fb027c
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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