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Methanol → HCID 16103460, 화합물

HRID 1513843
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HRID 1513843 반응식
[C:1]([C:6]1[S:13][C:12]2[C:11]3[S:14][C:15]4[C:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]CCCCCCC)=[C:18]([C:37]([O:39]CC)=[O:38])[S:17][C:16]=4[C:10]=3[S:9][C:8]=2[C:7]=1[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]CCCCCCC)([O:3]CC)=[O:2].CO.[OH-].[Li+]>O1CCCC1.O>[CH2:20]([C:19]1[C:15]2[S:14][C:11]3[C:12]4[S:13][C:6]([C:1]([OH:3])=[O:2])=[C:7]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:8]=4[S:9][C:10]=3[C:16]=2[S:17][C:18]=1[C:37]([OH:39])=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]
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참가 물질

6

반응물 3

HCID 887Methanol2회HCID 3939Lithium HydroxideHCID 67006721HCID 67006721, 화합물2회

생성물 1

HCID 16103460HCID 16103460, 화합물수율 98.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran
용매
2회

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온도
90 °C

실험 절차

Ester deprotection (Step C) The 2,6,-dicarboethoxy-3,7-diheptadecylthieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (5.00 g, 7.39 mmol) product of Example 6, was dissolved in tetrahydrofuran (THF) (280 mL) then methanol (40 mL) was added. Lithium hydroxide (707 mg, 29.5 mmol) was dissolved in water (7 mL) and added to the stirred methanol and THF solution. A condenser was fitted and the reaction mixture was heated in an oil bath at 90° C. for 16 hr. The THF and methanol were removed under reduced pressure. 60 mL of methanol and 10 mL of conc. hydrochloric acid were added then stirred for 4 h. Next 50 mL of water was added and the solid was filtered off. The product was dried under vacuum to give the 3,7-didecanyl thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene-2,6-dicarboxylic acid (4.50 g, 98% yield). 1H NMR (D8-THF)(of the di-lithium salt) δ 0.88 (6H, t, J=6.9 Hz), 1.20-1.47 (28H, m), 1.70-1.86 (4H, m), and 3.24 (4H, t, J=7.5 Hz).

후처리

  1. customA condenser was fitted
  2. customThe THF and methanol were removed under reduced pressure
  3. addition60 mL of methanol and 10 mL of conc. hydrochloric acid were added
  4. additionNext 50 mL of water was added
  5. filtrationthe solid was filtered off
  6. customThe product was dried under vacuum

출처 및 근거

ORD 기록
ord-a0efd2365d5d48b483405751b885ee82
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217183B2

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