tert-Butanol → HCID 69416176, compound

HRID 1351244Notes

Reaction equation

HRID 1351244 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[C:10](C(O)=O)[C:6]=2[CH2:5][CH2:4][CH2:3]1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>>[C:38]([O:42][C:19](=[O:28])[NH:16][C:10]1[C:6]2[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:7]=2[S:8][CH:9]=1)([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3860983STK279704

Product 1

HCID 69416176HCID 69416176, compound

Procedure

7-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid (18 g), 15.3 mL of triethylamine (15.3 mL) and 30.3 g of diphenylphosphoryl azide (30.3 g) in t-butyl alcohol (360 mL) were heat refluxed for 1 hour. After the organic solvent was removed by evaporation at reduced pressure, purification by NH silica gel column chromatography was carried out. Recrystallization from dichloromethane-hexane was carried out to provide the title compound (19.1 g) as a colorless crystal.

Workup

  1. temperaturerefluxed for 1 hour
  2. customAfter the organic solvent was removed by evaporation at reduced pressure, purification by NH silica gel column chromatography
  3. customRecrystallization from dichloromethane-hexane

Sources & evidence

ORD record
ord-18f6fe06cb7d44e2a72c39388ca5c44a
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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