Heptane → HCID 58224166, compound

HRID 402323Notes

Reaction equation

HRID 402323 reaction equation
O[C:2]1([C:12]2[C:20]([OH:21])=[CH:19][C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].C([SiH](CC)CC)C.CCCCCCC>COC(C)(C)C>[OH:21][C:20]1[C:12]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]2=[O:11])=[CH:13][C:14]2[O:18][CH2:17][O:16][C:15]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 12052TriethylsilaneHCID 58224171HCID 58224171, compound

Product 1

HCID 58224166HCID 58224166, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
10.5 °C

Procedure

A 1600 L reactor was charged with 3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one (113.1 kg, 396 mol), evacuated and filled with nitrogen. Trifluoroacetic acid (679 kg) was added in two portions over 20 minutes and the internal temperature was lowered to 10° C. over 1 h. Triethylsilane (69.2 kg, 595 mol) was added over 2 h 05 min at 10-11° C. and the mixture was stirred for a further 0.5 h at 10-11° C. A 1000 L reactor was charged with heptane (524 kg) and tert-butyl methyl ether (63 kg). The contents of the 1000 L reactor were transferred to the 1600 L reactor over 13 minutes at an internal temperature of 10-11° C. The resultant yellow-orange suspension was allowed to warm to 23° C. over 1 h. The solid was collected by filtration, washed with heptane (464 kg) followed by tert-butyl methyl ether (57 kg) and dried at 50° C. under a reduced pressure of 58 to 7 mbar over a period of 25 h to afford 3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one (82.8 kg, 75%) as an off-white solid: purity (HPLC-UV at 300 nm) 98.0% a/a; 1H NMR (300 MHz, DMSO-d6) δ 10.40 (s, 1H), 9.25 (s, 1H), 7.17-7.10 (m, 1H), 6.95-6.81 (m, 3H), 6.55 (s, 1H), 6.43 (s, 1H), 5.92-5.85 (m, 2H), 4.66 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 177.9, 150.1, 146.6, 142.7, 139.6, 130.9, 127.4, 123.8, 121.2, 115.9, 109.5, 109.0, 100.7, 97.8, 55.0.

Workup

  1. customevacuated
  2. additionfilled with nitrogen
  3. additionTrifluoroacetic acid (679 kg) was added in two portions over 20 minutes
  4. waitThe contents of the 1000 L reactor were transferred to the 1600 L reactor over 13 minutes at an internal temperature of 10-11° C
  5. temperatureto warm to 23° C. over 1 h
  6. filtrationThe solid was collected by filtration
  7. washwashed with heptane (464 kg)
  8. customdried at 50° C. under a reduced pressure of 58 to 7 mbar over a period of 25 h

Sources & evidence

ORD record
ord-ded3163a4ad7489a8f486a3583c2450b
Source dataset
uspto-grants-2014_06
Patent number
US08742109B2

Reaction notes

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